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Ellen Hancock 200484318 Context Bonds

The Thesis Antithesis and Synthesis of Practice –

The Thesis Antithesis and Synthesis of Practice – Context Bonds Practice In Context By Ellen Hancock 200484318 School of Fine Art, History of Art and Cultural Studies

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Contents Key

p.4

Thesis of Practice Context Bonds

p.7

Chapter 1

Introduction

p.12

Chapter 2

Thesis of OOH from Artistic elements (Ae)

p.15

Chapter 3

Thesis of OOOH from Scientific elements (Se)

p.22

Chapter 4

OOH formation via displacement, addition or

Chapter 5

rearrangement

p.27

Conclusion

p.32

Appendix

p.34

Antithesis of Practice – Context Bonds

p.63

Synthesis of Practice – Context Bonds

p.109

Chapter 1

Synthesis of thesis and antithesis

p.112

Chapter 2

Experiment of re - contextualisation

p.122

Chapter 3

Evaluation of results

p.141

Chapter 4

Conclusion

p.143

Bibliography

2

p.146


Ellen Hancock 200484318 Context Bonds

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Preface to thesis, antithesis and synthesis of Practice-Context Bonds

These three texts utilise the dialectic structure composed by Hegel of thesis, antithesis and synthesis. This method suggests that we begin with a thesis, an idea or theory and while exploring this thesis one always reaches a point of antithesis: negativity either in the form of a more superior thesis, realised faults with the thesis, or unavailable data. However by re –evaluating these stages and improving them, synthesis, can be achieved. The three texts within Practice-Context bonds aim achieve this process.

The three texts consider the creation of the OOH through bonding practice and its context. The OOH refers to the desired interaction from the audience when viewing the re- contextualised work

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Key for the Thesis of Practice – Context Bonds

A – Art

Activated- In reference to the “=OOH Exhibition”. This exhibition acts as the ‘test tube’ where the OOH reaction will occur

Ae – Artistic elements; the elements utilised by the artist. (In this document relating to: the white cube and signage, lighting, plinths and the audience.)

ASe2 –Artistic elements and scientific elements combined

C – Context

CO2 – Carbon Dioxide

Compound – Two or more elements combined to make a chemical substance

Dependent variable –human response, the OOH

Edirol – Portable recording device

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Independent variable – the variable that is changed in order to test the dependant variable. For example in this experiment it is solid CO2

OOH-The OOH refers to the desired interaction from the audience when viewing the reconceptualised work. The response more readily found in science when observing a scientific method.

ooh- refers to a lesser version of the above-mentioned OOH

P – Practice: relating the artists practice

P-C bonds – Practice in Context bonds

Re – contextualisation – A combination of scientific and artistic elements reconfigured to create an artwork. NB it is not merely a re- observation of scientific method, theory or material in an artistic setting

S - Science

Se- Scientific elements; the elements utilised by the scientist. Within this document relating to: the lab, equipment, scientific knowledge and the audience.

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Solid CO2 – Dry Ice

=OOH Exhibition: An exhibition presenting the three resulting pieces from experiments 1,2,3 and used to test the OOH. Pronounced as it sounds ‘equals OOH’. This exhibition acts as the ‘test tube’ where the OOH reaction will occur. The three experiments aim to create three final pieces that by the =OOH Exhibition are activated and the true reaction (the testing of the OOH) can occur. This is very important to note. Although three separate experiments are discussed in this piece, the reaction and the experiment will not be happening until the =OOH Exhibition.

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The Thesis of Practice – Context Bonds

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Ellen Hancock 200484318 Context Bonds

The Thesis Antithesis and Synthesis of Practice –

Note to reader

This document is written specifically replicating ‘The Synthesis of Carbon – Phosphorous Bonds, Second Edition.’1 This published text documents the progression during the continual formation of organic compounds2 created when the elements carbon and phosphorous bond together. It discusses new methods and advances within this production process. In this document ‘carbon’ has been replaced by ‘context’ and ‘phosphorous’ by ‘practice’, in an attempt to explore the products or compounds of bonding practice and its context using the same “scientific method”. However it is important to note this text is a thesis and not a synthesis like the original text; the aim is to achieve synthesis by exploring the experimental process used in the original published text. The intention of ‘Thesis of Practice – Context Bonds’ is to deliberately follow the form and structure of the original text as much as possible. The scientific language, cadence and writing style have been retained in order to echo the original tone and to underscore the connections between science and art.

1 Robert Engel, JamieLee LCohen, :The Synthesis of Carbon Phosphorous Bonds, 2

nd

Washington, D.C.: CRC press LLC 2004)

2 Two or more elements combined to create a chemical substance 8

Edition, (Boca Raton London, New York,


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The Thesis Antithesis and Synthesis of Practice –

Preface to the First Edition

Interest in the synthesis of P-C bonds was at one time only theoretical 3 and limited to a concern chiefly centered on other practitioners and their production methods. It did not reflect the individual P-C bonds of the artist or progress them particularly, it was too broad and often unrelated.

More recent developments however have delivered a clearer understanding of the progression towards P-C bond synthesis and the desired result - the OOH. Not only have there been new applications found for its production but these have also resulted in a wider more, responsive audience to activate the transformation and potential for OOH. We begin here with the thesis of P-C bonds aiming ultimately towards its synthesis.

The trained chemist assisting in these experiments has little knowledge of P-C bonds or accompanying literature. But this is not an attempt to educate them ( or anyone else) in relation to that. Instead it is through a performative collaboration and recontextualisation, that a greater understanding of P- C development is obtained in order to activate the viewer entirely as desired.

Abstract

3 The original P-C discussed participatory arts. Titled ‘The Invited Invaded and Ignored viewer in participatory arts’ it was purely art historical.

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This text is intended to provide a concise document outlining the process of analysis and discovery, leading to a greater understanding of the compounds formed by Practice – Context bonds. As a result the reader can follow the progression from initial stages through to an advanced view of approaches to P-C union.

The condition of the OOH has never before been investigated. It has advanced in parallel with the developing Practice. This document covers new approaches in obtaining the OOH, developed from further experimentation, into P-C bonds and their accumulation.

This work will be of use not only to the dedicated “Practicing Art Historian/Critic/Writer/Marker” but also to the practicing artist involved in creating their own Practice-Context bonds, using it as a resource for their developmental pursuits.

To this end it describes three experiments and their procedures. The first explores the artistic variables, the second the scientific variables and the third a collaboration between artist and scientist. All three experiments use solid CO2 as the independent variable and the aim was to create 3 final pieces to be exhibited in the =OOH Exhibition on February 21st 2013. The resulting works from of all three experiments will be activated at this exhibition. Experimental observations taken at the =OOH Exhibition are recorded in this document.

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These three pieces shown in an activated event, question the artist’s chosen method in obtaining the OOH compared with two more accessible, more adaptable, but less informative methods. It is intended to be not only a source of critical and annotated reference but also a working guide for the Artist in the Studio.

Chapter 1

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Introduction

1.1Desired advances in P-C bond formation

The OOH refers to the desire for interaction from the audience when viewing the recontextualised work. This response is commonly found in science when observing scientific reactions.

Interest in the creation of the OOH has continued to expand in recent years. This is a direct result of developing processes for Practice in numerous synthetic procedures as well as an understanding of the role of the elements in Context. There are elements of PC bonds that are well understood and have been known for quite some time as being vital to the P-C bonding process. An awareness of these elements and their qualities however does not necessarily inform a successful procedure. The three experiments discussed in this paper and their testing in the =OOH Exhibition aim to test whether P-C bonds can be formalized more effectively to create the OOH or whether Ae or Se have to be more readily accepted individually.

There is a desired result from ASe2, when they are combined on the one hand, the process can becomes a lot more sensitive, often failing, on the other success can be sporadic or occur without warning. Given that success can be found using Ae and Se separately, it is understandable to question why we would even consider combining the two when we know how to create the OOH using them separately inappropriate conditions. There is though a very good reason for this; separately Ae and Se using an

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independent variable receive an ooh, which is sufficient, but it tends to be transient and can only be obtained from certain environments depending whether or how Ae or Se is used. However ASe2 and subsequently what is currently understood to be the elements of P-C bonds creates OOH, the desired outcome.

It is important to note that this experiment to be activated at =OOH Exhibition does not aim for a conclusive answer; not only is that impossible, it is irrelevant. Testing an uncontrollable variable (human response) with the aim of formalisation is not achievable. A greater understanding of the process and outcomes is the intention.

1.2 Assessment of experiment results

There have been several ‘classical’ collaborations in regard to producing the OOH— activated in “MYR”, “Study Abroad Exhibition”, “No Sharp Objects”, “Dissemination”, and “The Great Escape” and soon to be shown in “£383,911.73”. It continues to be extensively examined in P-C bonds.

Other developments in current and potential applications of P-C bonded materials have spurred an even wider interest in the OOH. There is an expansion in the range of reaction types considered for P-C bond generation. Some of these are new developments on old approaches that were not previously encountered.

There is promising potential from the activation of experiments 1, 2 and 3 in the =OOH Exhibition. These three reaction systems will be activated in the =OOH Exhibition. This

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will allow a consideration as to which experiment system is the most successful and as a result provide further insights into the production of the OOH and therefore P-C bonds.

The results will be recorded using the Edirol system and assessed accordingly. Direct responses from participants will be gathered using a strictly predetermined set of questions. The questions will not allow for a discussion, only for reaction. The results will be discussed within this document.

1.3

Nomenclature problems in P-C bonds using scientific method

Nomenclature: the devising or choosing of names for things, especially in a science or other discipline.4

Quite often, nonsystematic nomenclature is used in the literature dealing with science and art. These results in unnecessary confusion - systematic nomenclature is easier to use and understand. Nomenclature based on the development and continuation of P-C bonds aims to unite S and A; to create a more considered response to them collaboratively. Similarly it aims to promote communication between both disciplines.

Chapter 2

4 (No Author) Definition of Nomenclature

(Online Dictionary) http://oxforddictionaries.com/definition/english/nomenclature?q=nomenclature [Accessed 1st March 2013]

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Thesis of OOH from artistic elements (Ae)

Experiment 1 preparation - Artistic elements

• The elements that provide an artistically fertile environment for an experiment. • Elements that facilitate the experience of art by re- observing scientific methods.

2.1Introduction Using artistic elements alone to create the OOH is an approach with both advantages and disadvantages. The advantages relate to availability; Ae are readily available in the current context and are often more appropriate within it. The disadvantages of using Ae instead of ASe 2 relate first to a lack of engagement between S and A. The use of Ae alone is conventional and can be utilised commercially as some prefer but using this method excludes the benefits ASe2 has to offer. Secondly it restricts the user, relying on them being a ‘square within a cube’. Finally, the reaction creates only an ooh where an OOH is achievable; the outcome must be as ‘capital’ as possible.

In this chapter, the Ae are considered and then the advantages of using Ae over Se or ASe2 are reviewed .The purpose here is to consider whether the OOH is still obtainable for the practicing artist venturing into a larger Context. The discussion is limited to the more- or-less direct synthesis of solid CO2 with Ae.

2.2.1 White Cube space/Signage

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The most predominately associated A environment and most commonly used.

'The highly controlled context of the modernist'5 white cube is composed of 'two, four, six sides'6 respectively. The term white is derived from its appearance, which is actually 'clean artificial -the space is devoted to the technology of aesthetics.' 7 'The gallery is constructed along laws as rigorous as those for building a medieval church. The outside world must not come in, so windows are usually sealed off. Walls are painted white. The ceiling becomes a source of light... The art is free, as the saying used to go, “to take on its own life.”8 ‘...In this context a standing ashtray becomes almost a sacred object.'9

An accompanying, additional influence, element, catalyst, reactor to the white cube space is signage. Its properties and potential can include: authority, trickery, deception, revelation, conclusion, untitled. Both can provide either a highly reactive or merely suggestive environment, sometimes there can be no reaction at all.

5 Brian O'Doherty ; introduction by Thomas McEvilley, Inside the white cube : the ideology of the gallery space(Berkeley, Calif. ; London : University of California Press, 1999),p.7

6 Ibid.,p.81 7 Ibid.,p.15 8 Ibid.,p.15 9 Ibid.,p.9 16


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2.2.2 Lighting Lighting in the white cube can be used to create a less reactive state by causing a condition of eternal refraction capable of being used with fewer interferences and distractions.

It can also be used within the white cube to generate, and focus the outcome of P-C bonds and create a more productive context. The reactivity of lighting can be increased when used in certain synthetic processes to create an effective (and occasionally deceptive) impression.

2.2.3 Plinths Plinths are not amorphous but precise. They exhibit quite high reactivity, when used in conjunction with the white cube space or lighting. Because a plinth has a distinct shape ‘literally... a pedestal’10 the resulting compound of P-C bonds is given a hierarchal position even more so than already established by the white cube space and lighting. The plinth can generate a safer environment for the practicing artist but this should be approached with caution, as it might be misleading, potentially a ‘prop’ and only safe with complete understanding of the process and where contextually necessary.

2.2.4 Audience The audience is the recipient of the experiment and creates the reaction, they are where the experiment occurs and they create the compound, the synthesis, the bond and the

10 (No Author) The Plinth Rejected: Minimalism (Online Arts Blog) http://www.fringeartsbath.co.uk/plinthby-plinth/ [Accessed 4th March 2013]

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OOH. The =OOH Exhibition allows the gathering of the human vessels in which the reaction takes place.

The receptivity of this audience will be directly related to reactivity. There is further potential to affect their sensitivity and therefore reaction; this research is on- going and in the early stages and is therefore uncorrelated.

The audience ‘is affected by a whole series of leant assumptions about art. Assumptions concerning: Beauty Truth Genius Civilization Form Status Taste, etc.’11 ‘Consciousness’12

Expectation

2.3Experimental procedures

11

John Berger, Ways of Seeing(London : British Broadcasting Corporation and Penguin Books, 1972), p.11

12 Ibid., p.11 18


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2.3.1 Materials -Camera -Container -Dry Ice -Gloves -Label -Plinth -Spot lightsx2 -Spoon -Water 200ml

2.3.2 Procedure Preparation of dry ice using the artistic elements is conducted under basic aqueous conditions. 1. ‘Always wear protective gloves whenever handling dry ice. Do not allow dry ice to touch bare skin. Dry ice in contact with skin may result in frostbite. Prolonged exposure will cause severe frostbite.’ 2. Collect Dry Ice from Mr. Pete Morton, bearing in mind storage instructions:

‘DO NOT handle dry ice with bare hands. It can cause severe cold burns and frostbite. Only experienced and properly instructed people should handle dry ice.

ALWAYS store dry ice in a properly designed container.

ALWAYS keep the container lid closed when not in use.

ALWAYS secure the container lid open before reaching in to unload the product. Avoid leaning into the container for longer than necessary.

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DO NOT store dry ice in any gas tight container. Within large containers, gas atmospheres will have built up.

DO NOT expose dry ice to high ambient temperatures unnecessarily as this increases the sublimation rate.

DO NOT store in cellars or unventilated rooms. ALWAYS Ensure adequate low-level ventilation wherever dry ice is stored.’ 13 3. Take all materials to the Photography Studio. 4. Place plinth centrally within the room. 5. Make sure room is completely clean. 6. Set up lights up and turn on. 7. Place bowl on plinth in central position. 8. Attach labels in prime locations on wall and on the façade of the plinth. 9. Place 3 tablespoons of Dry Ice one at a time into the container, remembering the safety precautions while doing so. 10. Add 500ml of water slowly to create an aqueous solution being extremely careful not to spill any out of the container. 11. Stir clockwise in two full circles to agitate the reaction. 12. Make observations at =OOH Exhibition where reaction will occur. Record as many participants as possible, asking the questions stated below in their intended order:

1. What have you encountered at the exhibition? 2. What reaction did you have? Did you expect to have a reaction? 13 (No Author) Safety (Commercial Dry Ice supplier)http://www.dryiceuk.com/safety [Accessed 18th March 2013]

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3. What did you expect the exhibition to be like? 4. What did you think of the exhibition?

2.4 Results Experiment 1 was set up ready for testing as can be seen below (Fig 1) however due to unforeseen events this experiment could not be activated and subsequently was not presented for observation in =OOH Exhibition. The scientific collaborator needed for experiment 2 and 3 and the completion of this document was unable to attend due to other commitments.

(Fig 1)

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Chapter 3 Thesis of OOH from Scientific elements (Se)

Experiment 2 preparation- Scientific elements.

•

The elements that allow the optimum environment for the successful execution of scientific exploration. Subsequently they facilitate the experiences of science.

3.1 Introduction This chapter explores if Se alone can create a more beneficial method. Using Se to create the OOH is an approach not previously researched This method comes with several disadvantages relating to availability; using this method relies upon a substitution; only the collaborating practising chemist was asked to perform this experiment. Within this experiment the adopted role is as observer within Se not as a practising artist. Roles and positions are questioned, as is the experiment; whether it is actually still a scientific experiment and whether it is in anyway genuine, authentic art practice.

In this chapter, the advantages of using Se over Ae or ASe2 are considered. The purpose here is to review whether the OOH is still obtainable for the practicing artist venturing into a larger Context. This discussion is limited to the more- or-less direct syntheses of solid CO2 with Scientific elements.

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3.2.1 The Lab The purpose of the laboratory is well known. It is an established synthetic utility where reactions are constantly occurring. It is constructed and utilised as a learning environment and is a place devoted to the acquisition of knowledge and testing of hypotheses.

In most instances there are set roles assigned not subject to displacement and only those belonging to the discipline can usually participate in laboratory activities. There are certain procedures that must be followed in the Laboratory context - for example safety measures must be adhered to and rules for the storage of equipment and materials.

3.2.2Equipment A variety of mechanistic investigations have been established that are assisted by the use of sophisticated advanced equipment. As a consequence experiments:

- Are more specific - Obtain quantifiable results - More controlled

This structured process tends to create alienation from other disciplines

3.2.3 Scientific knowledge:

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The practicing chemist is well versed in the properties and handling of solid CO2 (the independent variable) and also in the field of chemistry. This equates to a much more prepared, strategic and conventional application. The Chemist’s practice can be shared but relies on knowledge that cannot quickly be imparted and absorbed.

3.2.4. Audience The audience is the receptor of the experiment and creates the reaction, they are where the experiment occurs and they create the compound, the synthesis, the bond and the OOH. The =OOH Exhibition allows the gathering of the human vessels in which the reaction takes place.

The receptivity of the audience will be directly related to reactivity. There is a potential to affect their sensitivity; this research is on- going however and in the early stages therefore is discounted.

The audience is affected by a series of learnt assumptions about Science. Assumptions, for example, concerning: Knowledge Understanding Truth Genius Civilization Form Status

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Safety Progression

Expectation

3.3

Experimental procedure

Preparation of dry ice using Se is conducted under basic aqueous conditions

3.3.1 Materials

As yet unknown, it depends entirely upon the Scientist; complete control of this experiment and the materials used within it belongs to the Scientist. It cannot be predetermined. As previously stated solid CO2 will be utilised as the independent variable.

3.3.2 Procedure As yet unknown, it depends entirely upon the scientist; complete control of this experiment and the materials used belongs to the Scientist. It cannot be predetermined. As previously stated solid CO2 will be utilised as the independent variable.

As with Experiment 1 observations will be made at =OOH Exhibition where the reaction will occur. As many participants as possible will be recorded, asking the questions stated below in their intended order:

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1. What have you encountered at the exhibition? 2. What reaction did you have? Did you expect to have a reaction? 3. What did you expect the exhibition to be like? 4. What did you think of the exhibition?

3.4Results Experiment 2 could not unfortunately be set up for testing due to unforeseen events concerning safety issues As a consequence this experiment could not be activated and subsequently was not presented for observation in =OOH Exhibition. The collaborator needed for experiment 2 and 3 and the completion of this document was unable to attend due to other commitments.

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Chapter 4 P-C bond formation via displacement, addition, or rearrangement

Experiment 3 preparations – Artistic elements and scientific elements combined ASe 2

4.1 Introduction Practice – Context bonds by displacement reaction is historically significant within the development of the practice. This experiment has previously been favored as having the most productive results. Here the specific approach towards P – C bonds are reviewed noting the advantages and disadvantages of this contextually traditional method and also to contemplate the rationale for experiments 1 and 2. The results from this experiment are predicted to be more successful than 1 and 2, but the testing of all three leads to a more considered outcome.

4.2 Previous testing Previous experimental efforts namely ‘The origin of the OOH.2 and their nuptials’ (in this case using iron filings as the independent variable) were examined by the scientist Dr. Neil Thompson who collaborated with the artist to create it:

‘Encasing the pendulum magnets allowed them to interact without irreversibly sticking together. The six pendulums were therefore coupled albeit rather weakly. This allowed the driving force at the top of the pendulums to provide a stimulus without setting the pendulums in regular periodic

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motion; rather the interactions between pendulums gave rise to a chaotic non-repeating behavior which leant the piece a more organic and natural discourse in time. ‘

The magnets underneath the table polarized the iron filings enabling them to “stand-up” in the field. The extent to which the filings were extended and/or interacting with a passing pendulum depended on the relation orientation of the poles in the magnets underneath the table and those inside the pendulums. These interactions gave additional complexity to the piece. Of course, interactions between the magnets inside the pendulums and those under the table would also contribute to the dynamics. The reflective table and lighting arrangement served to highlight the structure of the filing islands to the audience. This was very effective.

Overall, the effect was quite mesmerising and the dynamic nature of the piece gave continued interest to the onlooker.’14

It is interesting to note that this review addresses the piece in two parts; firstly explaining how and why and only secondly seeing the context. The components are finally considered as artistic elements contributing to the whole piece. There is also a very specific language used in this text, a contemplation and intent to review both ‘parts’ of the piece.

It is noteworthy that from the opposing field it cannot be seen as a whole piece but a culmination of experimentation using ASe2.

14 Private correspondence via email between myself and Dr. Neil Thomas, teacher at The University of Leeds, School of Physics and astronomy. Permission granted.

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4.3 Elements

4.3.1 Discourse and exchange Discourse and exchange creates a linkage between A and S and have been useful in the development of P- C bonds. This method facilitates the linkage of the two fields in exploring an independent variable. It is important that communication occurs before experimentation is attempted, as the two methods of experimentation and the translation of results are very different. Collectively, an ongoing dialogue is beneficial.

4.3.2 Artistic elements The artistic elements (2.2) used in experiment 1 are referred to again in this experiment. For this experiment they are used less rigidly and are susceptible to displacement or rearrangement. They will only be used if of benefit to the final outcome.

4.3

Scientific elements

The scientific elements (3.2) used in experiment 1 are referred to again in this experiment. For this experiment they are used less rigidly and are susceptible to displacement or rearrangement. They will only be used if of benefit to the final outcome.

4.3.1 Audience

The range of reactions when displacement is involved will be further updated. Expected is a less secluded environment and an audience less restricted by the understanding

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from their perspective fields (considering specifically A and S again). Art with Se is unusual and transitory, a one off medium and experience. It creates a new context to craft with and that creates a new paradigm rather than being a clinical exploration for the discovery of facts. An OOH rather than ooh reaction from the audience is desired.

4.4

Experimental procedure

The preparation of dry ice combining Ae and Se will be conducted under basic aqueous conditions

4.4.1 Materials As yet unknown, it depends upon the discussions and deliberations made by the artist and scientist. It cannot be predetermined. As previously stated solid CO2 will be utilized as the independent variable.

4.4.2 Procedure As yet unknown, it depends upon the discussions and exchanges made by the artist and scientist. It cannot be predetermined. As previously stated solid CO2 will be utilised as the independent variable.

Again as with Experiment 1 and 2 observations will be made at =OOH Exhibition where the reactions will occur. As many participants as possible will be recorded, asking the questions stated below in their intended order:

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1.

What have you encountered at the exhibition?

2.

What reaction did you have? Did you expect to have a reaction?


Ellen Hancock 200484318 Context Bonds

4.5

The Thesis Antithesis and Synthesis of Practice –

3.

What did you expect the exhibition to be like?

4.

What did you think of the exhibition?

Results

Experiment 3 could not be set up ready for testing due to unforeseen events. As a result this experiment could not be activated and subsequently was not able to be presented for observation in =OOH Exhibition. The collaborator needed for experiment 2 and 3 and the completion of this document was unable to attend due to other commitments.

This renders the comparison and evaluation of the 3 approaches incomplete in the manner set out in this document.

P-C bonds are a synthesis of elements caused by a reaction and measured by the production of OOH. In any event of OOH production there is scope to discover other states in which C and P coexist and synthesize. This has led to further research into the occurrence of the OOH.

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Chapter 5 Conclusion 5.1 Conclusion Fig 1.4 15

Fig 1.5 16

Fig 1.617 Fig 1.718

Fig 1.819

15 Private correspondence via email to Pete Morton, Studio and Exhibitions technician The University of Leeds, Fine Art, History of Art and Cultural studies Fig 1.4

16 Ibid.,Fig 1.5 17 Ibid., Fig 1.6 18 Private correspondence via email to Pete Morton Fig 1.7 19 Ibid., Fig 1.8 32


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Fig 1.920

Appendix Text used from Engel, Robert, Cohen, JamieLee L, The Synthesis of Carbon Phosphorous Bonds, 2nd Edition, Boca ration, London, New York, Washington, D.C.: CRC press LLC 2004

-

Only parts of chapter 1, 2, 3 and 4 are used.

-

No images (referred to as figures) from the original text are used.

20 Ibid., Fig 1.9 33


Ellen Hancock 200484318 Context Bonds

SECOND EDITION Synthesis of Carbon–Phosphorus Bonds Copyright © 2004 by CRC Press LLC

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Ellen Hancock 200484318 Context Bonds

SECOND EDITION Synthesis of Carbon – Phosphorus Bonds

Robert Engel JaimeLee Iolani Cohen

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CRC PRESS Boca Raton London New York

Washington, D.C.

Copyright Š 2004 by CRC Press LLC

Preface to the First Edition Interest in the synthesis of organophosphorus compounds was at one time relatively limited, being of concern chiefly to those involved in the preparation of materials of certain commercial interest (e.g., insecticides, flame retardants, and detergents). With this situation existing, it has been relatively rare to find university courses being taught on the topic of synthesis of these materials. However, recent developments have made an understanding of organophosphorus compounds and their syntheses of significantly more general value. Not only have there been found applications for organophosphorus compounds in a wide range of commercial applications, but also these materials have become of great utility for the facilitation of other organic transformations. Yet, the university- trained organic chemist is provided with little guidance to the performance of organophosphorus chemical conversions or to the organophosphorus literature. It is in an attempt to provide direction to the organic chemist lacking specific training in organophosphorus chemistry that this book is presented. A major portion of the effort of preparing this manuscript was performed while I was on

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sabbatical leave from Queens College at the Rohm and Haas Company in Spring House, Pennsylvania. I wish to thank Queens College for the time and Rohm and Haas Company for their hospitality, both of which were important for this work. In addition, I would dedicate this work to my children, Cheryl and Erik. Robert Engel Copyright © 2004 by CRC Press LLC

Contents Chapter 1 Introduction 1.1

Recent advances in C–P bond formation 1.2

1.3

Information sources for C–P compounds

Nomenclature of C–P compounds

Chapter 2 Synthesis of organophosphorus compounds from elemental phosphorus 2.1 Introduction 2.2

Availability of elemental phosphorus 2.2.1 White phosp horus 2.2.2 Red

phosphorus 2.2.3 Black phosphorus 2.2.4 General reactivity 2.7

Experimental procedures

References Chapter 3 C–P bond formation using nucleophilic trivalent phosphorus reagents 3.1 Introduction 2.3

Attack on elemental phosphorus by nucleophiles

2.4

Radical attack on elemental phosphorus

2.5

Direct addition to systems

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Oxidative additions with olefins

2.7.1 Preparation of tris(2-carbamoylethyl)phosphine oxide — Preparation of a tertiary phosphine oxide from white phosphorus under aqueous basic conditions 2.7.2 Preparation of phenylphosphine — Preparation of a primary phosphine from white phosphorus with an organometallic 2.7.3 Preparation of 〈-hydroxy-p-methylbenzylphosphonous acid — Preparation of a phosphonous acid from red phosphorus in aqueous medium 2.7.4 Preparation of benzylphosphonic acid — Preparation of a phosphonic acid from red phosphorus in aqueous acid 2.8 3.2

Substitution reactions using neutral trivalent phosphorus reagents

3.2.1General 3.2.2 Mechanism 3.2.3Reagents 3.2.3.1 Trialkyl phosphites, dialkyl alkylphosphonites, and alkyl dialkylphosphinites 3.2.3.2 Triaryl phosphites, diaryl alkylphosphonites, and aryl dialkylphosphinites 3.2.3.3Silyl esters of phosphorous, phosphonous, and phosphinous acids 3.2.4 Recent advances 3.3

Substitution reactions using anionic trivalent phosphorus reagents

3.3.1 General

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3.3.2 Mechanism 3.3.3 Reagents 3.3.4 Recent advances 3.4

Preparations of 〈-substituted phosphoryl compounds

3.4.1 General 3.4.2 Neutral trivalent phosphorus addition to unsaturated carbon 3.4.3 Anionic trivalent phosphorus addition to unsaturated carbon 3.4.4 Recent advances 3.5

Conjugate addition reactions

3.5.1 General 3.5.2 Neutral phosphorus reagents in conjugate additions 3.5.3 Anionic phosphorus reagents in conjugate additions 3.5.4 Recent advances in addition to conjugated and unconjugated olefinic sites 3.6

Experimental procedures

3.6.1 Preparation of trisodium phosphonoformate — Reaction of a chloroformate with a trialkyl phosphite and cleavage of the ester linkages 3.6.2 Preparation of tris(trimethylsilyl) phosphite — Preparation of a silyl ester of a trivalent phosphorus acid for Michaelis–Arbuzov reaction 3.6.3 Preparation of 2,3-dioleoyloxypropylphosphonic acid — Reaction of an alkyl halide with a silyl phosphite ester 3.6.4 Preparation of dimethyl (4-methoxybenzyl)phosphonate —

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Reaction of a benzyl halide with a trialkyl phosphite 3.6.5 Preparation of 5-(3-benzoylpropionyl)-3-deoxy-3diisopropoxyphosphinylmethyl-1,2-di-O-acetyl-D- ribofuranose — Reaction of an alkyl bromide in a carbohydrate series with triisopropyl phosphite 3.6.6 Preparation of triethyl 2-phosphonobutanoate — Reaction of a trialkyl phosphite with a 2-halocarboxylate ester 3.6.7 Preparation of 1-isopropoxy-2-methylpropylphosphonate — Reaction of a trialkyl phosphite with a 1-chloroether 3.6.8 Preparation of diphenyl benzyloxycarbonylaminomethanephosphonate — Reaction of a triaryl phosphite with an N-acetoxymethyl- carbamate generated in situ 3.6.9 Preparation of diethyl isobutyrylphosphonate — Reaction of a trialkyl phosphite with a carboxylic acid chloride 3.6.10Preparation of (diethyl phosphonomethyl) acetyl sulfide — Reaction of a trialkyl phosphite with a 1-halosulfide 3.6.11Preparation of diethyl 1-oxo-2-(3-indolyl)ethanephosphonate — Reaction of a trialkyl phosphite with a carboxylic acid chloride in solution 3.6.12Preparation of 1-ethoxybenzylphosphonate — Reaction of a trialkyl phosphite with an acetal in the presence of boron trifluoride 3.6.13Preparation of 1,10-diphenyl-1,10-diphosphacyclooctadecane 1,10dioxide — Reaction of an alkyl halide with a phosphinite ester

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generated in situ by reduction of a phosphinate 3.6.14Preparation of diethyl 3,5-di-t-butyl-4hydroxybenzylphosphonate — Reaction of a benzylic acetate with a trialkyl phosphite 3.6.15Preparation of diethyl 3,3-diethoxypropynyl-1-phosphonate — Reaction of a sodium salt of a dialkyl phosphite with an acetylenic halide 3.6.16Preparation of bis-(2,2-dimethyltrimethylene)yl [(2,5- dimethyl1,4-phenylene)dimethylene] diphosphonate — Reaction of the sodium salt of a cyclic phosphite diester with a bis-benzylic halide 3.6.17Preparation of di-n-butyl N,Ndiethylcarbamoylmethylphosphonate — Phase transfercatalyzed reaction of a dialkyl phosphite with an alkyl chloride 3.6.18Preparation of [1-(diethoxyphosphinyl)ethoxy]dimethyl- silane — Reaction of an aldehyde with a trialkyl phosphite in the presence of a silyl halide 3.6.19Preparation of O,O-diphenyl 2-methylthio-1-(Nphenylthioureido)ethylphosphonate — Reaction of triphenyl phosphite with an imide generated in situ in the presence of acetic acid 3.6.20Preparation of 1-aminoethane-1,1-diphosphonic acid — Reaction of phosphorous acid with a nitrile 3.6.21Preparation of N-benzyl -aminobenzylphosphonic acid —

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Reaction of phosphorouss acid with an imine 3.6.22Preparation of benzyliminodimethylenediphosphonic acid — Reaction of phosphorous acid with a formaldimine generated in situ 3.6.23Preparation of diethyl 1-(trimethylsiloxy)octylphosphonate — Reaction of a mixed silyl–alkyl phosphite with an aldehyde 3.6.24Preparation of (SP)-t-butyl(phenyl)(〈-hydroxybenzyl) phosphine oxide — Reaction of a chiral secondary phosphine with an aldehyde under basic conditions 3.6.25Preparation of diethyl (S)-〈-hydroxybenzylphosphonate — Reaction of an aldehyde with a dialkyl phosphite facilitated by a chiral BINOL complex 3.6.26Preparation of 1-aminobutyl-1,4-diphosphonic acid — Reaction of an aldehyde with a triaryl phosphite in the presence of a thiourea 3.6.27Preparation of diphenyl 1-(benzylcarbamoyl)-4- (phthalimido)1-phosphonate — Reaction of a phthalimido- protected aminoaldehyde with a triaryl phosphite in the presence of benzyl carbamate 3.6.28Preparation of ethyl methyl(2-carbomethoxy-3phenylpropyl)phosphinate — Addition of a monobasic phosphinous ester to an unsaturated ester in the presence of a silylating agent

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3.6.29Preparation of 2-dimethoxyphosphinyl-2-methoxy-2phenylacetaldehyde oxime — Reaction of an unsaturated nitro compound with a trialkyl phosphite in the presence of an alcohol 3.6.30Preparation of 3-diethoxyphosphinyl-2-methylpropionamide — Addition of a monobasic trivalent phosphorus acid to an unsaturated amide in the presence of an alkoxide base 3.6.31Preparation of di-n-butyl di-n-butoxyphosphinylsuccinate — Addition of a monobasic trivalent phosphorus reagent to an unsaturated ester in the presence of base 3.6.32Preparation of phenyl(mesitylyl)(-cyanoethyl)phosphine — Addition of a secondary phosphine to an unsaturated nitrile under aqueous basic conditions 3.6.33Preparation of 1-ethoxy-2-phenyl-4,5-dimethoxycarbonyl- ∆2⎣ 5-phospholene 1-oxide — Reaction of a vinylicphos- phonite diester with an unsaturated carboxylate ester 3.6.34Preparation of phenyl (-carbomethoxyethyl) phosphine– borane — Reaction of a primary phosphine– borane with an unsaturated ester References Chapter 4 C–P bond formation via displacement, addition, or rearrangement 4.1 Introduction 4.2

Phosphorus–halogen compounds

4.2.1 General 4.2.2 Generation of the phosphorus–halogen linkage

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4.3

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Substitution reactions on phosphorus–halogen compounds

using organometallics and related reagents 4.3.1 General 4.3.2 Types of organometallic reagents 4.3.2.1 Organomercury reagents 4.3.2.2 Organolead compounds 4.3.2.3 Grignard reagents 4.3.2.4 Aluminum-based systems 4.3.2.5 Organocadmium reagents 4.3.2.6 Organotin reagents 4.3.2.7 Lithium reagents 4.3.2.8Enamines 4.4

Addition reactions of P–H compounds

4.5

Addition reactions of P–Cl compounds

4.6

Rearrangements resulting in the formation of new P–C bonds

4.7

Experimental procedures

4.7.1 Preparation of diallyl phosphorochloridate — Preparation of a dialkyl phosphorochloridate from a dialkyl phosphite by the Todd reaction 4.7.2 Preparation of 2-chloromethyl-2-ethyl-1,3-propanediol phosphorochloridate — Preparation of a dialkyl phosphorochloridate by reaction of a trialkyl phosphite with chlorine 4.7.3 Preparation of isopropyl methylphosphonochloridate —

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Preparation of a phosphonochloridate by reaction of a phosphonate diester with phosgene 4.7.4 Preparation of diethyl 3-trifluoromethylphenylphosphonate — Reaction of a Grignard reagent with a dialkyl phosphorochloridate 4.7.5 Preparation of vinyldichlorophosphine — Reaction of phosphorus trichloride with an organomercury compound 4.7.6 Preparation of n-butyldichlorophosphine — Monoalkylation of phosphorus trichloride using an organocadmium reagent 4.7.7 Preparation of diethyl 3-diphenylthiophosphoryl-2- morpholino1-cyclohexenylphosphonous acid — Reaction of an enamine with a phosphorus halide and subsequent esterification 4.7.8 Preparation of bis(4-methoxyphenyl)phenylphosphine oxide — Reaction of a Grignard reagent with a phosphorus halide 4.7.9 Preparation of diethyl 1-hydroxy-2-butynephosphonate — Reaction of a phosphorus halide with a 2-alkynol and subsequent rearrangement to generate a hydroxyphosphonate 4.7.10Preparation of 2-[1,3]dithianyldiphenylphosphine oxide — Reaction of a chlorophosphine with a stabilized carbanion reagent 4.7.11Preparation of 2,5-dimethylbenzenephosphinic acid — Aluminum chloride-mediated reaction of phosphorus trichloride with an aromatic hydrocarbon 4.7.12Preparation of (1-aminopropyl)phenylphosphinic acid — Reaction of a carbonyl compound with benzyl carbamate and a dichlorophosphine

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4.7.13Preparation of diethyl 5-methoxytetrahydrofuran-2ylphosphonate — Reaction of an acetal with a phosphorochloridite 4.7.14Preparation of propadienylphosphonic dichloride — Rearrangement of a propargylic trivalent phosphorus ester 4.7.15Preparation of 2-chlorohept-1-ylphosphonic dichloride — Reaction of an alkene with phosphorus pentachloride 4.7.16Preparation of 6-amino-1-hydroxyhexylidenediphosphonic acid — Reaction of a carboxylic acid with phosphorous acid and phosphorus trichloride 4.7.17Preparation of diethyl 1-(4-pyridyl)-1,2-dihydropyridine- 2phosphonate — Reaction of phosphorus trichloride with a pyridylpyridinium chloride References

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Abstract The present effort is intended to provide an update of the earlier edition, bringing to the chemist in concise form advances in the approaches to C–P bond formation previously discussed, as well as several other aspects of C–P bond formation. These latter aspects include the generation of organophosphorus compounds from elemental phosphorus (of particular industrial interest for purposes of cost containment); advances in the preparation of phosphoranes, including the use of transient oxophosphoranes as intermediates in organophosphorus compound syntheses; and new approaches toward the preparation of compounds with aromatic and vinylic carbon–phosphorus bonds. As with the prior edition, this work will be of use not only to the dedicated “phosphorus chemist” but also to the practicing chemist who only occasionally is involved with organophosphorus chemistry, using it as an aspect of other synthetic pursuits. To this end, it contains numerous experimental examples from the literature with added notes from the authors’ own experiences in utilizing these reactions. It is intended to be not only a source of critical and annotated references but also a working guide for the

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chemist in the laboratory.

Chapter 1 Introduction 1.1 Recent advances in C–P bond formation Interest in the preparation of organophosphorus compounds has con- tinued to expand in recent years. This is a direct result of developing applications for phosphorus compounds in numerous synthetic pro- cedures as well as an understanding of the role of the element in biological systems. The several “classical” efforts in regard to applications of organophosphorus compounds — the preparation of insec- ticides, agricultural chemicals, flame retardants, medicinal agents, and reagents for olefination reactions — continue to be highly active topics in organophosphorus chemistry. However, other developments in applications and potential appli- cations of carbon– phosphorus bonded materials have spurred an even wider interest in organophosphorus chemistry. Several of these areas of developmental activity are noted here. Significant potential is promised for the performance of stereospecific syntheses through the use of chiral diphosphorus reagents associated with metals. Numerous reaction

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systems have been noted involving such species facilitating asymmetric induction. For exam- ple, BINAP systems (Figure 1.1) have been studied as catalysts for asymmetric carbon–carbon bond formation, and similarly, MiniPHOS (Figure 1.2) for asymmetric hydrogenation processes. Additional synthetic investigations should be conducted to press the advantages such species promise for facile production of chiral organic products, containing or not containing phosphorus themselves. Similarly, P- chiral monophosphorus species have demonstrated potential for stereospecific C–P bond formation in association with transition metal species. In recent years, the potential for phosphorus-containing den- drimers and related materials to serve as templates for themodification of surfaces has been explored and promises to provide access to designed nanostructures. An example of such species is the second- generation phosphorus dendrimer (Figure 1.3) with a C–P bond at the core. Recent years have also seen the development of a variety of com- plexation reagents incorporating C–P bonds and their associated functionalities, such as phosphoryl linkages. For example, substituted calixarenes (Figure 1.4) have been developed for extraction of radio- nuclides, and phosphorus-derivatized cyclodextrins for stereospecific inclusion interactions. With these developments of applications for organophosphorus compounds, more powerful synthetic approaches toward their syntheses have similarly been sought and found. In the following chapters, we revisit some of the older approaches toward C–P bondformation, noting recent advances and providing exemplary experimental procedures. In addition, we are expanding the range of reaction types considered for C– P bond generation. Some of these are new developments on old approaches that were not reviewed in the prior edition of this work. Others are fundamentally new

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approaches that allow facile preparation of organophosphorus compounds avail- able previously only with significant difficulty. Prior to considering synthetic approaches toward C–P bond formation, we review two areas related to the literature of organophosphorus chemistry that are of particular value to those chemists who do not focus primarily on phosphorus. 1.2 Nomenclature of C–P compounds Quite often, we find nonsystematic nomenclature used in the literature dealing with organophosphorus compounds. This results in unnecessary confusion, as systematic nomenclature is easy to use and understand. Nomenclature based on the oxidation state of the phosphorus center eliminates the confusion and helps to promote under- standing of the chemistry as well as to facilitate communication. Table 1.1 shows structures for tricoordinate and tetracoordinate phosphorus compounds related to oxyacids with their English general names. Also noted are the names for simple esters of the parent acids. They are organized based on oxidation state and the number of bonds of the carbon– phosphorus type. At times, confusion arises in noting oxides of primary and sec- ondary phosphines (Figure 1.5). These species participate in equilibria much as the phosphonous and phosphinous acids do and can be named as types of phosphonous and phosphinous acids.

The tetracoordinate phosphorus species related to the oxyacids may be considered to be pentavalent. (For nomenclature purposes we will consider the phosphoryl group, P=O, to be an ordinary double bond.) A variety of tetracoordinate phosphorus compounds that are also clearly tetravalent are common. With four carbon groups (alkyl, aryl, olefinic, or acetylenic) attached to phosphorus, the phosphorus bears a positive charge

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and these species are simple phosphonium salts (Figure 1.6A). When ligands are attached to phosphorus through atoms other than carbon, the term quasiphosphonium ion is generally applied (Figure 1.6B). These species exhibit certain chemical and physical characteristics quite similar to those of ordinary phospho- nium cations but often also bear special reactivity. For example, the oxyphosphonium species involved as intermediates in the Michae- lis–Arbuzov reaction are referred to as quasiphosphonium species. Pentacoordinate phosphorus compounds are generally referred to as phosphoranes (Figure 1.7) or oxyphosphoranes depending on the absence or presence of oxygen linking directly to the phosphorus. Wittig reagents, while generally involving coordination of phospho- rus to only four ligands, are also often referred to as phosphoranes. 1.3 Information sources for C–P compounds This section is organized as an annotated listing of compendia for data relating to techniques used in organophosphorus syntheses, characteristics of organophosphorus compounds, and mechanisms of reactions of organophosphorus compounds. While not exhaustive, these references provide working chemists with additional sources of data useful for the performance of their efforts with organophospho- rus compounds. (We will be excused if we begin this list with our own review works in this area.) Synthesis of Carbon–Phosphorus Bonds, Engel, R., CRC Press, Boca Raton, FL, 1988 — The first edition of the current work, it presents a survey of methods for forming carbon– phosphorus bonds with detailed examples to the date of publication. Handbook of Organophosphorus Chemistry, Engel, R., Ed., Marcel Dekker, Inc., New York, 1992 — Contributed chapters are con- cerned with particular types of reactions of organophosphorus compounds, industrial applications of them, and their spectro-

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scopic characteristics.

New Aspects in Phosphorus Chemistry I, Majoral, J.-P., Ed., Springer- Verlag, Heidelberg, Germany, 2001 — Contributed chapters are concerned with recent advances in a wide range of areas in phosphorus chemistry. The Role of Phosphonates in Living Systems, Hilderbrand, R.L., Ed., CRC Press, Boca Raton, FL, 1983 — Contributed chapters sur- vey the role of naturally occurring organophosphorus com- pounds (containing a C–P bond) in biological systems and the use of a wide variety of organophosphorus compounds for the regulation of metabolism and the treatment of disease. Aminophosphonic and Aminophosphinic Acids, Chemistry and Biolog- ical Activity, Kukhar, V.P. and Hudson, H.R., Eds., John Wiley & Sons, Chichester, England, 2000 — Contributed chapters deal with syntheses and biological activity of compounds in the title categories. Methoden der Organischen Chemie, Vol. 12 (Parts 1 and 2), Sasse, K., Ed., Georg Thieme Verlag, Stuttgart, Germany, 1963; continued in Methoden der Organischen Chemie — Supplement, Vols. E1 and E2, Regitz, M., Ed., Georg Thieme Verlag, Stuttgart, 1982 — This major work is particularly concerned with the methods of syntheses of organophosphorus compounds and derivatives of phosphorus oxyacids. The work is organized according to structural type and provides extensive detailed preparations for numerous representative compounds (in German). Organophosphorus Compounds, Kosolapoff, G.M., John Wiley & Sons, New York, 1950; continued in Organic Phosphorus Com- pounds, Vols. 1–7, Kosolapoff, G.M. and Maier, L., Wiley-Inter- Science, New York, 1972–1976 — These works attempt to be encyclopedic (to date of publication) in

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reporting preparations and characteristics of organophosphorus compounds. Topics in Phosphorus Chemistry, Vols. 1–11, Grayson, M. and Griffith, E.J., Eds., Wiley-InterScience, New York, 1964–1983 — This series has contributed chapters concerned with individual types of reactions, mechanisms, and spectroscopy of phospho- rus compounds. Copyright © 2004 by CRC Press LLC

Chapter 2 Synthesis of organophosphorus compounds from elemental phosphorus 2.1 Introduction Using elemental phosphorus to prepare compounds containing the carbon–phosphorus bond is an approach with both advantages and drawbacks. The advantages relate to availability of the elemental material; elemental phosphorus is readily available in a condition of high purity and at a relatively low cost. The disadvantages of using the most reactive form of elemental phosphorus, “white phosphorus,” relate first to its high reactivity toward oxygen; it ignites in ordinary air at temperatures above 34 C. ̊ Other forms of elemental phosphorus are less reactive toward oxygen but are correspondingly less reactive in desired processes as well. Further, when elemental phosphorus is used to prepare organophosphorus compounds, fundamental difficulties of several types arise. In this chapter, we first review the nature of the several forms of elemental phosphorus and then proceed to consider their uses for specific types of syntheses of compounds containing the car- bon– phosphorus bond. Prior reviews have also been concerned with these topics.1,2 Our purpose here is to update these presentations and provide

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fundamentals for the practicing chemist venturing into the use of elemental phosphorus. We limit this discussion to the more- or-less direct syntheses of organophosphorus compounds from elemental phosphorus. We will consider reactions that generate monophosphorus species without C–P bonds as critical intermediates, provided that these intermediates may be converted to organophosphorus compounds in a “one-pot” process. We will not review processes in which elemental phosphorus is initially converted to a species that must first be isolated and purified prior to use in C–P bond introduction. 2.2 Availability of elemental phosphorus 2.2.1

White phosphorus

Early investigations3–6 of this fundamental form of the element deter- mined that (in the vapor phase) it is composed of tetraatomic units (P4), with the phosphorus atoms held in a tetrahedral array containing six equivalent phosphorus–phosphorus bonds (Figure 2.1). Calculations7 indicating that the unshared electron pairs on each phosphorus atom are held in 3s orbitals led to an understanding that the bonding in this molecule is much akin to that of carbon atoms in cyclopropane rings. Bonds within the tetrahedron are relatively weak, owing to poor orbital interactions, and are cleaved with relative ease. The term “white” is derived from its appearance, which is actually a very pale yellow. Generally stored under water, in which it has negligible solubility and with which it is inert, this form of elemental phosphorus possesses a waxy surface and has a relatively low melting point (44.1 C) ̊ with a specific gravity of 1.82. As noted, although it is inert toward water, this material is extremely reactive toward oxygen, igniting in ordinary air at 34 C. ̊ This characteristic commonly produces difficulties in handling the material in the open atmosphere. Transfer and weighing of the material often pose problems. (One approach to alleviating some of this difficulty — which is not necessarily recommended

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by the authors involves storing the material under acetone, which will evaporate rapidly and cool the white phosphorus during transfer.) Toxicological characteristics and handling procedures have been summarized.8 Analysis for elemental phosphorus by chromatographic means has been described.9 The existence of three equivalent bonds to each of the phosphorus atoms, which must be broken in the formation of mono-phosphorus organophosphorus compounds, might appear to be a problem at first; all must be broken as new bonds are being generated to phosphorus. However, the fundamental approaches toward the use of white phosphorus accomplish this necessary action with relatively few extraneous reaction processes. 2.2.2 Red phosphorus Upon heating to 400 C, ̊ white phosphorus is converted to red phosphorus, a material somewhat less reactive with oxygen and capable of being used with fewer difficulties. In this treatment, a portion of the P–P bonds within the tetrahedra are broken, and new P– P bonds linking (former) tetrahedral units are generated, yielding chains of phosphorus units (Figure 2.2). Although the reactivity of red phosphorus is decreased from that of white phosphorus, it remains useful in certain synthetic processes. 2.2.3 Black phosphorus Black phosphorus may be either amorphous or crystalline. It exhibits quite low reactivity, both with oxygen and other reagents, compared to white or red phosphorus, and is stable in air. Because it has a puckered shape, the phosphorus remains tricoordinated in black phosphorus and crystallizes in sheets in a way similar to the behavior of graphite. Black phosphorus is generated from white phosphorus either by heating under pressure or in the presence of mercury. It is of relatively little value for

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the synthesis of organophosphorus com- pounds. 2.2.4 General reactivity Although black phosphorus is generally inert, red phosphorus and particularly white phosphorus are capable of undergoing reactions to generate organophosphorus compounds. Several different sets of conditions may be used to form C–P bonds from elemental phospho- rus. These will be discussed in the following sections. 2.7 Experimental procedures 2.7.1

Preparation of tris(2-carbamoylethyl)phosphine

oxide — Preparation of a tertiary phosphine oxide from white phosphorus under aqueous basic conditions28 A solution of 10 ml of 10 N aqueous KOH diluted to 25 ml with absolute ethanol was added dropwise over a period of 30 min to a well-stirred mixture of 0.4 g-atom (12.4 g) of finely divided white phosphorus, 1.2 mol (85.2 g) of acrylamide, and 200 ml of absolute ethanol under a nitrogen atmosphere. The temperature was main- tained at –5 to 0 C ̊ by a cooling bath. After stirring for an additional 45 min, the white solid generated was recovered by filtration. This solid was dissolved in 125 ml of hot glacial acetic acid, and the solution was cooled to room temperature. (Any unreacted white phosphorus could be removed at this point by decantation under a nitrogen atmosphere.) The solution was filtered through diatomaceous earth, diluted with 600 ml of absolute ethanol, and cooled at 5 C ̊ for 30 min. The resultant white solid was collected by filtration, washed with absolute ethanol, and dried to produce the pure tris(2carbamoylethyl)phosphine oxide in 74% yield. 2.8 Summary We have not been concerned with an attempt to be encyclopedic here. Rather, we are looking to provide: 1. Reference to processes that are known to provide

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organophosphorus species in reasonable yield from elemental phosphorus 2.

Reference to processes of potential value for the preparation of orga-

nophosphorus species from elemental phosphorus In the first instance, we must note the processes generating phos- phine (PH3) from the elemental substance in aqueous basic medium to be a useful approach with particular types of substrates with which PH3 (or the derived PH2–1 anion) can act as a nucleophile. Production of a particularly desired type of organophosphorus compound is clearly dependent on both the substrate and the nature of the solvent. In the second instance, two approaches seem to be worthy of special note. The synthetic utility of elemental phosphorus based on it acting as a radical trap appears to be quite valuable, but additional effort is required to determine the variability of the source of the organic free radicals. (Is there some other, more efficacious, source of organic free radicals that works better with this system than acylated N-hydroxy- 2-pyridones?) The other approach that appears ripe for development is the hydrolysis/elimination with “phosphorates” derived from the oxidative addition of white phosphorus to alkenes. We look forward to the continued development of such facile approaches toward the preparation of fundamental phosphonic acids. References

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Chapter 3 C–P bond formation using nucleophilic trivalent phosphorus reagents 3.1 Introduction The use of an electron-rich trivalent phosphorus center for addition to or substitution at an electrophilic site is a long-established approach to the formation of carbon– phosphorus bonds. The classical studies of the Michaelis–Arbuzov, Michaelis–Becker, Abramov, Pudovik, and related reactions and their mechanisms and synthetic utilities have been thoroughly reviewed. In this chapter, we present only a brief introduction to these reactions and provide several examples of their more facile uses from the older literature. More attention is given to relatively recent developments regarding such reactions that are seen as improvements in their general utility. Of particular note is the application of such reactions for the preparation of organophosphorus compounds bearing heteroatom substitution at the 〈-carbon site (carbon of the C–P bond). Herein we review the approaches to this intriguing category of compounds, with some discussion of their applicability to probing and modifying metabolic processes. This topic has also received recent review, and we survey the

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available review literature along with the original reports. 2.2 was mimicked once again here for 3.2 3.6 Experimental procedures 3.6.1 Preparation of trisodium phosphonoformate — Reaction of a chloroformate with a trialkyl phosphite and cleavage of the ester linkages32 Triethyl phosphonoformate was prepared by the dropwise addition of ethyl chloroformate (10.85 g, 0.1 mol) to triethyl phosphite (16.6 g, 0.1 mol) with vigorous stirring at ambient temperature. After the had subsided, the volatile materials were removed under reduced pressure and the residue vacuum distilled to give pure triethyl phosphonoformate (17.2 g, 82%) of boiling point (bp) 86 to 88 C/0.25 ̊ torr, which exhibited NMR, infrared (IR), and mass spectra in accord with the proposed structure. To the resultant triethyl phosphonoformate (105 g, 0.5 mol) was added sodium hydroxide solution (250 ml, 10 M) over a period of 15 min at ambient temperature. The solution became hot, and ethanol by-product boiled off from the reaction mixture. Upon cooling, a precipitate formed, which was recrystallized from water to give col- orless crystals of the pure trisodium phosphonoformate hexahydrate (27.5 g, 19%), which exhibited IR and NMR spectra and x-ray crystal analysis in accord with the proposed structure. References

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Chapter 4 C–P bond formation via displacement, addition, or rearrangement 4.1 Introduction The use of organometallic species, either as primary reagents or as catalytic adjuncts, for the generation of carbon–phosphorus bonds by displacement reaction is historically significant. Of increasing importance today is the use of transition metal complexes for displacements and additions. This latter aspect has already been discussed briefly in Chapter 3, but is noted again here. We also review other approaches toward C–P bond formation, including additions to unsaturated link- ages and rearrangements of P–O–C linkages to P–C linkages. As in prior chapters, we review historically significant approaches toward C–P bond formation, noting the advantages and disadvantages of classical approaches, contemplate the more recent advances, and consider the opportunities associated with each. Detailed experimental procedures for examples of each of the types of reactions are provided. We begin, however, with a brief consideration of a group of phosphorus compounds of

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significance for their utility in the formation of carbon–phosphorus bonds via reaction with organometallic reagents in displacement reactions. 4.7 Experimental procedures 4.7.1 Preparation of diallyl phosphorochloridate — Preparation of a dialkyl phosphorochloridate from a dialkyl phosphite by the Todd reaction9 To a stirred mixture of diallyl phosphite (32.4 g, 0.20 mol) and carbon tetrachloride (35 ml, 0.40 mol), cooled to 0 C̊ , triethylamine (3.2 ml, 0.023 mol) was slowly added. The temperature was maintained at 0 C̊ for 1 h, during which time a vigorous reaction ensued. After this time, the reaction was allowed to come to room temperature and was stirred overnight. The precipitate that had formed was removed by filtration, hydroquinone (0.5 g) was added, and the solvent was evap- orated under reduced pressure at room temperature. The residue was vacuum distilled (65 C/4 ̊ torr) to give pure diallyl phosphorochlori- date (8.5 g, 22%). References

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The antithesis documents the publicity for the =OOH Exhibition.

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Locations Page: 2. Twitter page EXHIBITION

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3. Website http://equalsoohexhibition.info/ 4. Email via Jenny Coup (Education Service Officer for School of FAHACS) to FAHSCS School 6. Old Mining Building main notice board 7. Old Mining Building Level 2 notice board 8. Old Mining Building Level 1 notice board 9. Old Mining Building fabrication wall 10. Old mining Building, left column at entrance 11.Old mining Building, right column at entrance 12. Old Mining Building door to studios 13. 5/7 Lifton Studio’s main notice board 14. 5/7 Lifton Studio’s main door 15. 5/7 Lifton Studio’s main door to studio’s 16. 5/7 Lifton Studio’s door to lower level studio 17. 5/7 Lifton Studio’s back of main door to studios 18. 5/7 Lifton Studio’s inside lower level studio 19. 5/7 Lifton Studio’s door to upper level studio’s 20. 5/7 Lifton Studio’s project space 21. 4 Lifton Studio’s door by stairs to first floor 22 .4 Lifton Studio’s back of front door 23. 4 Lifton Studio’s top of first floor stairs 24. 4 Lifton Studio’s Debut Series, top floor 25. Leeds University Union notice board at main entrance 1 26. Leeds University Union notice board at main entrance 2

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27. Leeds University Union opposite Essentials 28. Leeds University Union common room notice boards 29. Leeds University Union wall next to Hidden café 30. Leeds University Union opposite Sesame 31. Leeds University Union notice board at back entrance to the Old Bar 32. Leeds University Union notice board at the front entrance to Old Bar 33. Megal café opposite the Parkinson Building 34. Pickards Tea Room opposite the Parkinson Building 35.Miro café opposite the Parkinson Building 36. Bakery 164 opposite the Parkinson Building 37. Chemistry basement notice board 38. 1st year studios, studio 1, Chemistry basement 39. 1st year notice board chemistry basement 40. 1st year studios, studio 2, chemistry basement 41. 1st year studios, studio 3, chemistry basement 42. Chemistry building 1st floor notice board 43.Chemistry building 2nd floor notice board 44.Chemistry Building 4th floor notice board 45. Chemistry Building 3rd floor notice board 46. Chemistry building notice board, exit to Parkinson building

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Bonds

Preface to the synthesis Since the =OOH Exhibition did not happen as planned, this document “The synthesis of Practice – Context Bonds” could not be written without further development of the

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Practice. As the aim is to maximise the production of Practice–Context bonds creating the OOH, the nature of the ongoing research is to re-contextualize the practice. This led to the development of the Antithesis to the original Thesis and then the Synthesis as the new context for the evolving practice. This document also appropriates the language and style of the Thesis but again re- contextualising it where necessary.

Abstract

The present text is intended to provide a concise document concerning the realisation of

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what it is that constitutes the elements of Practice – Context bonds and to bring to the reader the particular form of advances in the approach to P-C union since the development of the thesis and antithesis. New approaches to obtaining the OOH as developed from further experimentation are discussed, and the development of P-C bonds. To that end this document sets out a re-consideration of the thesis and provides a response to the problems with its procedures. This discussion firstly explores which elements truly dictate the current formation of P-C bonds. The result creates an experiment that allows the activation of the =OOH Exhibition in its new form. These observations are recorded in this document. This new experiment and its results show the required re –consideration in order to progress the thesis and antithesis therefore creating a true synthesis. It shows a determination to not simply return to the original thesis, and abandon eventual synthesis. Instead it is a consideration of the true elements at play, the writer’s situation within them and what is currently, as a result of this process the genuine synthesis at this moment in time.

Chapter 1 Synthesis of thesis and antithesis 1.1Advances

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P-C Synthesis is a proposal that requires rigorous testing, in that ‘For a hypothesis to be a scientific hypothesis, the scientific method requires that one can test it’ 21 In this situation there is no physical evidence to test the thesis or antithesis and no mathematical or quantifiable evidence to evaluate. The term “hypothesis” is no longer necessary in the search for synthesis; a new language has been deemed more appropriate. To explore and find synthesis further research and re - contextualisation is needed.

Art and science are united in their quest for making the invisible, visible. Each searches for ways to reach into the unknown and present new knowledge and experience. Not why, but how, the world works. As human beings we have the desire to make sense of what is around us both visible and invisible and subsequently how we respond to it. As previously stated the OOH is being used as a measure of that human response. In any event of OOH production there is scope to discover other states in which C and P coexist and synthesize.

The experiment so far has prepared the creative environment for OOH production using either Ae or Se or ASe2. Due to uncontrollable events, the addition of time as an unexpected variable, the experiment could not be activated and subsequently was not presented for observation in =OOH exhibition. However, the vital element, the thing of interest, the OOH is still available for investigation, if the practice has the possibility of re -contextualisation. What is now needed is art to visualise the =OOH exhibition.

21 (No name)Definition of Hypothesis (Wikipedia) http://en.wikipedia.org/wiki/Hypothesis [Accessed 12.01.13] 112


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Therefore the exhibition =OOH is not cancelled; rather it did not happen on Thursday the 21st February 2013. The oxford dictionary states that to cancel something is to: ‘decide or announce that (a planned event) will not take place…abolish or make void.’ 22 It exists in anticipation and as such will impact upon people and is available to create an experience within them, so the potential to produce the OOH is still there, if ways to measure it can be found. Currently no one knows except for Harriet Wiseman, Pete Morton, Emma Rushton and Andy Goddard (the chosen scientist who cancelled the event) that this event is no longer actually happening in it original form. There are 45 posters around the campus and the area surrounding it, a website, a twitter page and an invitation has been passed around the whole of the FAHACS School. As far as everyone else is concerned it is an event in anticipation. The information on the website states: ‘=OOH is an Exhibition examining the relationship between art and science. The three works exhibited are the result of three experiments questioning how artists and scientists work independently and collectively. Cardice looks at how the artist responds to scientific theory using ‘Artistic elements’ Untitled 2 places the emphasis on the scientist as creator using the ‘scientific elements’ Untitled 3 is collaboration. All works utilise Dry Ice as the independent variable.’

22 (No name)Definition of Cancelled (Oxford online dictionary) http://oxforddictionaries.com/definition/english/cancel?q=cancelled [Accessed 20.2.13]

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This is what they think they will see; this is what they are anticipating, an event combining art and science. I am required to heighten the atmosphere of anticipation, thus maximising the likelihood and quality of OOH production.

I enjoyed the trickery of lying and performing immensely, much more than I thought I would. I was worried that if people caught me off guard I would give something away and become flustered revealing everything in the heat of the moment. Actually on reflection I feel played the part rather well. People would ask me more of what it was about and I would tell them not much more than was said on the website replying slyly that they would have to wait and see, there would be no point coming if they knew everything. I even disappeared for a day pretending to work with Andy Goddard (the scientist). My accomplices’ Ms Wiseman and Pete Morton laid several deliberate rumours about my whereabouts; just to “stir the pot” a little more. I even bumped into someone at lunch that had heard this rumour and was curious as to how it was going. I replied with enough glee and balanced worry to seem suitable. Though maybe I didn’t bump into them and I am lying to you. It was all so much fun I could carry it on forever. However time dictates that I cannot. I had to cancel the exhibition on Tuesday two days before the planned exhibition.

Another (thrilling) alternative would have been to continue to have the exhibition, to have everyone arrive to nothing, to record and reflect on this reaction. I would not have been there myself, but I would have left a note and some recorders well hidden. My absence would have been an added component to the experiment, I would have been there in a form and their true feelings would be all the more accurate. It would have

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increased the hype and anticipation even further creating a stronger reaction from the deceit. It is interesting to ponder what reaction this situation would have activated, whether it would have been disappointment, annoyance or simply ambivalence.

This is not the event I planned; it is a different event but it is an event, that occurred in the time and place that =OOH was scheduled to happen. An event that evokes a reaction; not the intended one but perhaps a much more interesting one altogether. This is re – contextualisation. When time restricts you, re – contextualise. Perhaps I am enjoying this a little too much!

So, because I cannot re- contextualise completely the way I want to I will re – recontextualise, no one says I can’t, this is art not science. That is the beauty of art. The exhibition will re –exist in the form of interviews. These interviews will activate the exhibition and expose the resulting reaction.

1.2Assessment of the Thesis results The Uncontrollable Variable This is not the first edition of part two, it has been written, re – written and re – written again from the re – writing, it has then been re – contextualised and re- re – contextualised, discarded then begun again. It is 141 days since the 27 th of September and the first meeting for Practice in Context, there are 27 days until it is due in, it is 85 days since the first draft of 3000 words was handed it, I began my degree 1,246 days ago and I will finish it 133 days. Dictated by time; the endless countdown of this master has dictated everything. There have been 1,246 days of doubt that will remain ever thus.

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The true uncontrollable variable in this Practice in Context, the thesis, antithesis and synthesis, is not human response, not the OOH; it has and always will be time. I have to answer to it; it is unstoppable.

Time has a personality a voice, a say, a hand in my practice; it is the true judge, the real dictator of my practice in context. Time finds it all quite hilarious. Never one to play fair, time joins the game whenever and at whatever point it so wishes. My practice is shaped, and I am restricted by the scientist lack of time, I am restricted by what time deems as possible. Time is a natural force, an element, THE dimension and the ordering of everything.

However I am conscious of time, I cannot be ignorant in this relationship and play the victim. I know I am not restricted, not really, only if I give up. It is uncontrollable but I have to and can respond within it. It is universally accepted that time can only move in one direction, ‘The Arrow of Time dictates that as each moment passes, things change, and once these changes have happened, they are never undone.’ 23 But they can be learnt from.

I am not using the hand of time to excuse; I am not looking for a reason, quite the opposite. What I am acknowledging is that time adds an uncontrollable variable and that my realisation of this has allowed me to consider other avenues of exploration. I

23 ‘Destiny’ Wonders of the Universe, BBC 2, 6 116

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began with one question; I did not limit myself to that question producing results. My practice evolved and I asked more questions I did not expect to stick to the first question I chose as my guiding question, nor the second or third. Actually I would be quite worried if I did. Progression and development is not simple it is not structured but the development of my practice is constant, always, always constant. It does not always make sense, it is not always logical but it is always moving forward and therefore so is the context. And therefore context is not constant. For everything to run smoothly for 10,000 words, perfectly structured, neatly compiled over 168 days, each month adding a little more would be a failure - not a failure that taught me something but a Failure, (capital F), because it wouldn’t have taught me anything. I am not saying this is wrong and those that have done so have failed, I am not talking about anyone else here. I am talking about I.

I have to allow myself to be defeated by the elements in order to find a path through them. I surrender to the only thing that is consistent and that is change.

In the same way the thesis was affected by time not by scientists, or access or any other elements but the unstoppable nature of time. The exhibition, the event, and the experience related to it was not cancelled but required a re- consideration of the time and the availability within it.

1.3 Language

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The thesis mimics the document Synthesis of Carbon Phosphorous Bonds 24 25. This text was deliberately chosen for its obvious resemblance to Practice in Context. Firstly and most importantly, the title; Carbon Phosphorous bonds are literally as the name suggests, the bonds formed between Carbon and Phosphorous elements. Likewise as practice in context explores the bonds between my practice and the context within which it takes place. In the original abstract it explains that the text intends to explore the different formations of these bonds and their varying advantages and disadvantages, precisely what we would hope to achieve through the practice in context process.

In the original thesis the structure of the text of Synthesis of Carbon – Phosphorus Bonds 26is also used throughout for its symbolic connection to Practice in Context. The ease with which it could be translated into the three experiments and the =OOH Exhibition was remarkable and consequently in some ways quite humorous. I personified the text as much as was possible without losing the intent of what I was trying to say. This method provided a very accessible and productive structure. One that allowed for a methodical and almost formulaic approach and I believe worked perfectly for its purpose.

I played with the abbreviations and language used in the text avidly and enjoyed, for example, how easily Art and Science could be conditioned to the symbols A and S and practice in context P-C without losing substance. Not only this but satirical connections

24 Robert Engel, JamieLee LCohen, The Synthesis of Carbon Phosphorous Bonds, 2

nd

Edition, (Boca ration, London, New

York, Washington, D.C.: CRC press LLC 2004 )

25 It mimics it frustratingly so. There are laborious multiple introductions and a slow highly controlled method that creates extensive repetition and probably highly annoyed the reader!

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were found throughout enabling the original language to be used with only minor changes. I enjoyed this process immensely. When I looked back into the text for the synthesis I found how it could be further linked and with more humour. Within this text, the synthesis, I can re – consider the areas that were before measured as unnecessary, for example the actual procedure and functions of the original text.

Commercially Carbon Phosphorous bonds are used for ‘insecticides, flame retardants, and detergents’, products used to prevent something dangerous taking over, to make something clean and clear and to kill unwanted pests. One could say this is a preventative or a careful consideration of what is not needed and or hazardous. It is a controlling of elements, an awareness of the presence of something and having the knowledge and means by which to prevent it happening. Through the development of Practice in Context one often learns what is needed for their practice by the inverse what is not needed; what the hazards might be and how to prevent or remove them.

If we return to the abstract of the original text again it states that the text considers the ‘advances in the preparation of phosphoranes’27 one of the main compounds formed from carbon- phosphorous bonds. Phosphoranes are predominately used in practice of organophospherous chemistry28 (which in the thesis is equated to the practicing of art). What is interesting with phosphoranes when considering the synthesis is their molecular

27 Ibid.,p.16 28 As defined by the Oxford Dictionary Online, the study of ‘synthetic organic compounds containing phosphorus, especially pesticides and nerve gases of this kind.’ (No Name) Definition of Organophosherous (oxford online dictionary) http://oxforddictionaries.com/definition/english/organophosphorus?q=organophosphorus [Accessed 28 th February 2013]

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geometry, how they are constructed. The text was originally examined for its obvious connections to practice in context including its structure but if we look further into its research we find that actually the clues were already there for the synthesis...perhaps! Below is the molecular geometry of phosphoranes:

R1 R2 P

R3

R4 R5

‘This is the first class of compounds for which there is no accumulation of data obtained with other elements on which one may rely to provide analogies and working hypothesis.’29 The compound contains five substituent’s30 which here have been referred to as R. Each of the five bonds may attach to a different element and the bonds will differ in energy and strength. However until these bonds are formed we cannot obtain a ‘useful interpretation’ of their consequences. From ones practice several re – considerations or re – contextualisation’s are made. All resulting from the current practice, P, but not always evolving or developing in the manner one might expect. In this formation, phosphanes are unstable and need to attach to something else to become stable. The most productive and available element for them to bond with is Carbon,

29William E McEwen, Darrell Berlin K, Organophosphorus stereochemistry Part Two P(V) Compounds, (Stroudsburg, Pa : Dowden, Hutchinson & Ross ; [New York] : distributed by Halsted Press, c1975.),p.115

30 ���an atom or group of atoms taking the place of another atom or group or occupying a specified position in a molecule’(No Name) Defintion of Substituent (oxford online dictionary) http://oxforddictionaries.com/definition/english/substituent?q=substituents [Accessed 28 th February 2013]

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context. Much like Practice – Context bonds, much re – contextualisation’s have occurred and have consequently re -shaped the practice, but until context is properly realised in relation to the practice, it is not stable.

It is very important to acknowledge the relationship between Art and Science but also to accept it as relationship and a union. The two cannot be combined into a whole. They work well side by side and are at times completely correlative but it is important to realise when one field is catalysing the practice or, more importantly, inhibiting it.

Interestingly, =OOH has a duality in its interpretation this became apparent in conversation with participants surrounding the event. It can be read as it sounds but also elementally as equals O O H, referencing a scientific term or the elements themselves. This is a perfectly acceptable reading, as I designed the poster to this effect, to clearly reference the scientific link. OOH as elements would be Oxygen, Oxygen, Hydrogen. However as a scientific formula this would be written O2H.Even more interestingly this element cannot exist in any form not physically or energetically because oxygen is too electronegative to form such a compound. OOH cannot exist in science, it is not possible but it can it art.

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Chapter 2 Experiment of re-contextualisation 2.1 Introduction The experiment conducted for the attempted synthesis aims to re-contextualise the three experiments and =OOH Exhibition from the thesis, into the field of art where it can exist, thrive and thus synthesize. Here the OOH can be produced and measured.

The event and subsequent pieces could not be made because the scientific collaboration was halted on the grounds of safety. I could have conducted all three experiments myself, played the role of scientist, become a performer, but I do not want a reaction from my performance I want a reaction from the compounds of Practice – Contexts Bonds. I could have continued to have the exhibition but this would render the thesis void. It would be an antithesis to which there would be no thesis and hence nothing would be available for any synthesis. Yet if we evaluate it again in an artistic manner, PC is able to coexist and synthesise.

In this experiment we explore for the first time a new reaction. It has always previously been about creating an OOH, literally as it sounds, an almost childlike excitement. By advertising, a hype for the exhibition =OOH was created; anticipation, perhaps even the OOH itself (almost certainly encouraged by the title of the exhibition =OOH). This hype was encouraged as much as possible. However this is not the reaction tested in this experiment. Instead it is the removal of this anticipation; disappointment (one would hope). In this experiment several people are interviewed firstly about their anticipation

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of the event, and then their feelings and thwarted expectations after being told that actually it is no longer happening as planned. This experiment aims not only to resolve the issues concerning the thesis but also to develop my practice and therefore the context within which it is situated. Procedure 2.2 Materials -Set of ten prepared questions - Edirol (including charged batteries, and an SD card) -Interviewee (does not have to be a student) 31

2.3 Method 1. Posters due to be marked with the sign ‘The exhibition this Thursday (21.2.13) is no longer happening’ at 2.30pm on 19.2.13, find all available interviewees before this time. 2. Once with an interviewee, take them somewhere private, so as not to alert any other potential candidates to the news. 3. Before beginning to record, they are told they are being recorded and asked their permission to be quoted. 4. Tell them, that it is not a discussion, they will be asked questions and any questions asked to you will be ignored unless completely necessary. 5. Turn Edirol on and start recording. 6. Ask them these questions. It is very important to use the exact wording: 1. Have you heard about the exhibition =OOH? …if no read the website blurb.

31 Interesting to note here that two students were specifically approached to be interviewed, agreed and on the day cancelled due to other commitments.

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2. Do you know what it is about? 3. Are you intending to go? 4. Are you looking forward to it? 5. Unfortunately the exhibition this Thursday (21.2.13) is no longer happening. 6. Are you disappointed? 7. What did you expect to encounter in the exhibition? 8. What reaction did you expect to have? Did you expect to have a reaction? 9. What did you expect the exhibition to be like? 10. What did you think of the exhibition?

Results Participant 1 1. Have you heard about the exhibition =OOH?

Yes

2. Do you know what it is about?

No um…I have an idea because I’ve seen your work but um I don’t know what to expect.

3. Are you intending to go? Yes

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4. Are you looking forward to it?

I am, I’m quite excited to see what it will be I’ve been excited by the work I’ve seen you do before so…

5. Unfortunately the exhibition this Thursday (21.2.13) is no longer happening.

REALLY???

6. Are you disappointed?

YES!! (Laughs) I really wanted to go.

7. What did you expect to encounter in the exhibition?

I don’t know something that would either surprise me or intrigue me um something that I could interact with or play with almost but yeah…

8. What reaction did you expect to have? Did you expect to have a reaction?

Um I expected to be surprised almost marvelled not fairground attraction but yeah something like this

9. What did you expect the exhibition to be like?

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Umm I thought it would be quite scientific looking since it was in chemistry building experiment and things I could try out so.

10. What did you think of the exhibition? What did I think? I thought it would be a kind of crossover of science and art yeah. Felt positive about it though that I wanted to see it that I wanted to go.

After questions…

Ohhhhhhhhh (laugh loudly, almost awkwardly) I was really looking forward to it.

It could no longer physically happen…

Really? DAMM IT! I wanted to go (Laughs) I was looking forward to it. I thought ooh I'm gonna see the chemistry building and ooh there’s gonna be art there. I thought it would be like ahh I don’t know like a really good fun exhibition if you can call it that yeah. Damm it.

Are you going to do a different one?

Yeah

That’s good. I want to come see that one. Like everywhere I’ve gone I’ve seen it and its been like not a teaser campaign but like ooh I really want to go to this now, its in my mind that its gonna

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happen…Because there was not so little information but because it was…I really didn’t know what to expect but the name of it made me feel like I would enjoy it whatever it was.

How come?

I don’t know cos it was ooh I guess the sound just makes you, reminds you of all the times you experienced something that makes you ooh. So it had, that positive relation and I still don’t know what it is but I want to see it (laughs) so yeah…

Participant 2 1. Have you heard about the exhibition =OOH?

Yes, I have

2. Do you know what it is about?

Mm not entirely. It’s an artistic experiment or a scientific experiment or an art exhibition that uses scientific methods…I think!

3. Are you intending to go?

Yes

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4. Are you looking forward to it? Yes. Pause…Kind of ambivalent because I’m terrified of doing anything that isn’t practice in Context at the moment (both laugh)

5. Unfortunately the exhibition this Thursday (21.2.13) is no longer happening. Ohh

6. Are you disappointed?

…YES! (Laughs) Yes that feels kinda mean (both laugh) But I am also very curious as to whether it was planned to not happen anyway…

It can no longer physically happen

Or whether it’s just part of an experiment. (Laughs)

7. What did you expect to encounter in the exhibition?

Some kind of… well actually you in a white coat behind some science table. In a lab acting out some kind of experiment. Actually no not you doing something but some kind of live event where we cant see what you doing. No to be necessarily be interactive but to be engaged in some way.

8. What reaction did you expect to have? Did you expect to have a reaction?

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To be engaged like I said I suppose. To go ooh.

9. What did you expect the exhibition to be like?

As I said.

10. What did you think of the exhibition?

I couldn’t go could I? No! It was great marvellous! (Extremely sarcastic tone, even slightly annoyed)

Participant 3 1. Have you heard about the exhibition =OOH?

Yes

2. Do you know what it is about?

No

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3. Are you intending to go?

Yes

4. Are you looking forward to it?

Yes

5. Unfortunately the exhibition this Thursday (21.2.13) is no longer happening.

Ok

6. Are you disappointed?

Yes, I would have liked to see it.

7. What did you expect to encounter in the exhibition?

Ahhh, I saw on your cover photo a sort of cold ice thing going on… that the only kind of visual image I have or what could possible be going on there so that could be…

8. What reaction did you expect to have? Did you expect to have a reaction?

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I expected to have an OOH!!!...Reaction (laughs)

9. What did you expect the exhibition to be like?

Ummmm…um…Impressive (laughs)

10. What did you think of the exhibition?

Well I didn’t go did I!... well I dunno…uh…not much.

Participant 5 1. Have you heard about the exhibition =OOH?

Yes, I did

2. Do you know what it is about?

Um, I guess it’s about your collaboration with the chemistry

3. Are you intending to go?

Yes

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4. Are you looking forward to it?

Yes I do, of course

5. Unfortunately the exhibition this Thursday (21.2.13) is no longer happening.

Ok, it’s a shame

6. Are you disappointed?

YERR!

7. What did you expect to encounter in the exhibition?

Umm, I expected to see I don’t know an experiment from you, something with dried ice. What the poster kind of explained.

8. What reaction did you expect to have? Did you expect to have a reaction?

Umm… I guess being amazed (laughs) I hope say yeah!

9. What did you expect the exhibition to be like?

I don’t know no

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10. What did you think of the exhibition?

Umm I thinks it’s a really good thing to have a collaboration with another department and that your research goes so far and yeah.

After questions…

I Guess you can see it as an experiment as well, so the experiment failed. Experiments have different ways of… different aims…

Participant 6 1. Have you heard about the exhibition =OOH?

Yeah

2. Do you know what it is about?

Uhh science and art

3. Are you intending to go?

Yeah

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4. Are you looking forward to it?

Kinda yeah

5. Unfortunately the exhibition this Thursday (21.2.13) is no longer happening.

Is that a joke?ok…

6. Are you disappointed?

Well I bit I spose I was kinda curious

7. What did you expect to encounter in the exhibition?

I heard rumours about dry ice and some sort of crazy chemistry experiments and that’s alwaysquite fun to watch and to see it from a different perspective and an artist’s perspective is always interesting

8. What reaction did you expect to have? Did you expect to have a reaction?

Umm…like eh. I was expecting some kind of like club esq smoke everywhere and maybe like lights refracting through the smoke. I wasn’t sure but something like that.

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9. What did you expect the exhibition to be like?

Like I said before.

10. What did you think of the exhibition?

I didn’t go to it!?

Participant 7 1. Have you heard about the exhibition =OOH?

Yes

2. Do you know what it is about?

It’s err… a collaboration with the science department

3. Are you intending to go?

Yes

4. Are you looking forward to it?

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Yes, I’m looking forward to seeing it.

5. Unfortunately the exhibition this Thursday (21.2.13) is no longer happening.

Why?

It can no longer physically happen.

Really?

Yes

6. Are you disappointed?

Yeah (laughs)

7. What did you expect to encounter in the exhibition?

Some Dry Ice.

8. What reaction did you expect to have? did you expect to have a reaction?

When I saw it. Uhh I wouldn’t know until I saw it what kind of reaction I would have.

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9. What did you expect the exhibition to be like?

Something in the chemistry department. But I wasn’t… I was only sure of what you would provide to it, which was in the form of dry ice I assumed. But not what the other people would provide.

10. What did you think of the exhibition?

I don’t know cos I haven’t attended it.

After questions…

What!? Are you gonna do anything instead or…?

Yeah

So is there an exhibition?

Not this Thursday.

Ok, so we don’t come on Thursday

No

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Ok

Participant 8

1. Have you heard about the exhibition =OOH?

Yes

2. Do you know what it is about?

To be honest no.

The website blurb is then read out.

3. Are you intending to go?

If I can, I would like to.

4. Are you looking forward to it?

I always look forward to seeing students work. Especially yours Ellen!

5. Unfortunately the exhibition this Thursday (21.2.13) is no longer happening.

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Oh!...That’s a shame

6. Are you disappointed?

Umm yes cos…do you want me to tell you why?

Yes go ahead.

Well I guess I am very interested… I have not had a chance to catch up with all the students who went abroad and just see what you…what you’ve come up with now you come back from your experience, yunno it was quite a while ago now. So, in that sense yeah I am interested in what you did last year, it will be very interesting. Especially with your works as it is connected to my particular specialism I suppose.

7. What did you expect to encounter in the exhibition?

The science and art ties, crossovers is something that I would of expected on past form for to have done something about…with.

8. What reaction did you expect to have? Did you expect to have a reaction?

Well my reaction would be tied up with um my professional investment in all my students you particularly as the member of the study abroad group. Someone who in a sense I’ve been responsible for helping, helping to go and do something last year which would have influenced

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your work. So umm I would have been…my reaction might have been, would have been either sort of…um…well it might have been sort of disappointed I spose, I’d hope I wouldn’t have been. Umm…or pleased, pleased that you’d done something that was good and that way would feel that I’d been vindicated as a teacher, as a tutor

9.What did you expect the exhibition to be like?

Umm…(Pause)…ambitious with a slightly chaotic or kind of ad hoc edge to it.

10. What did you think of the exhibition?

(Long pause)…I thought it was really good, I kinda, really liked the untitled two in particular, I thought it really gave me an insight into the relationship of scientific method and the creative approach of artists. I think some of the technical side could have been smoothed off a little better and the presentation…um… had some slight rough edges…um but I’d rather see work that ambitious and um intelligent and those um other things can be ironed out and er er but I do think they need paying attention to.

Chapter 3 3. 1 Evaluation of Results

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Maximising the anticipation of the event was necessary, yet as time was required to spread the information on the updated posters, so collection of results was restricted to candidates who were available for interview on Tuesday 19 th of February between 9am and 1pm. This also meant that all but one of the candidates were students who knew me specifically and my practice. This strongly affected the results; these results were produced in accordance to the participant’s relationship to me. In this way I was a performer, the resulting reaction was created from my previous performances as a person and an artist. It was successful however in revealing what the expectation of me as an artist were and how I am perceived. I was pleased to see most of the results parallel my intentions.

The required recording and permission needed also affected the responses of the candidates. Perhaps it would have been better to not have told the candidates that they were being recorded or allow for a more fluid conversation. Although I believe it worked more effectively as a strict set of questions as it relied wholly on the candidate’s interpretation of the questions. There is most definitely room for more testing on the mode of assessing such an experiment.

It could be argued that this experiment in the end gave in to utilising only the artistic elements. Yet, the publicity of the =OOH Exhibition created the scientific elements. The original location (a lab in the chemistry building) and the title =OOH, established the scientific elements and the anticipation for them. There was no actually work to view, no solid CO2 but there was an awareness of its presence even if it wasn’t there at the time of

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interviewing. The result was collaboration, not with a scientist but of art and science specifically using the elements of each field spoken about in the thesis.

This experiment once again resulted in the conclusion that ASe 2 is the most productive method for the production of Practice – Context bonds and its resulting compounds at this time. Nevertheless ASe2 was combined in a completely new way, never tested before. The results from both experiments highlight the limits of the two fields of Art and Science, their contexts. However both experiments offer greater understanding into the two fields and their subsequent relationship when united.

The experiment also unexpectedly furthered the research into sensitising the viewer. Interest in this was mentioned in thesis but as being in the very early stages, now because of this re – contextualisation a natural progression of the OOH has occurred. Most viewers said in their interviews that they expected an OOH or something similar, when realising they wouldn’t an alternate reaction was received, disappointment. As the presenter, there was a parallel experience; that of disappointment at not being able to deliver the original events, having to seize the disappointment and recreate a new context out of it.

Chapter 4

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4.1 Conclusion An artist’s talk by Corinne Silva was recently held at the University. Her artwork was about landscape and our relationship to it. She spoke of the way our world, its environment and landscape, affects us and how we too affect it. ‘Imported landscapes’, a piece made by her in 2010 consisted of three photographs of the Moroccan landscape on billboards in the landscape of southern Spain. She told us that, due to the climate in that area of Spain, it never rained. However, very unusually, on the very night the photographs were put up, it did rain. The result created a modified photograph uniquely affected by the environment and landscape that she was in. The picture was shown to us in the talk, but simply for comical reasons. I found this infuriating. Nature, the nature she was specifically responding to, physically reacted with and influenced her work and she chose to ignore it. To me this work was by far the most interesting piece she shown, but in dismissing it, she ignored the elements that influenced, and indeed played a vital part in her creative practice.

In the text ‘The Artist’s Body as Gravity Makes Itself Its Master’ 32 Seth Kim Cohen discusses whether the artist Bas Jan Ader who used gravity as an artistic medium is defeated by gravity, or whether by accepting gravity and its control over him, he became the master of it. ‘His pieces are wilful experiences of failure’ 33 but it’s knowing this that’s what make them successful. It is by knowing his position within the element that he can react and work with it.

32 Seth Kim Cohen, ‘The Artist’s Body as Gravity Makes Itself Its Master’ Open Systems Symposium, Tate Modern, London, 2005 < http://www.kim-cohen.com/Assets/Texts/Kim-Cohen_Bas%20Jan%20Ader%20(2005).pdf > [Accessed 28th February 2013]

33 Ibid.,p.7 143


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Although it was not included as one of the original variables in the thesis, time has played an unyielding part in my practice and is most certainly an artistic medium in itself too. In accepting that I can engage with it, it becomes my creative ally. It requires me to update my practice and re-contextualize it.

Cohen coins the term “conceptual competence”. He explains that to be ‘certified conceptually competent, a representation must past two tests: first it must recognise the fact that mechanical competence is a fiction; second, it must make use of this knowledge.’34

Creativity calls for constant re-contexetualisation, inviting change and consequently growth; not labelling unexpected turns of events as ‘failures’, but rather opportunities for evolution in a determined creative response.

The original thesis was merely a starting point, a context for my practice at that time. Allowing the full and inevitable development of that particular P-C bond, taking into account all variables, known and unknown, called upon the resources of my own creativity and led to an unexpected form of synthesis. It has been shown that the OOH is always available; the challenge is to find a way to bring it into being. The layers of re-contextualization required in moving from thesis to antithesis to synthesis, confirm that synthesis does not denote an end point: quite the opposite, its allows the cyclical motion of creativity to continue.

34Seth Kim Cohen, ‘The Artist’s Body as Gravity Makes Itself Its Master’ p.6 144


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It is nine days until Practice in Context is due in. The time is 1.28 pm. The thesis, antithesis and its synthesis shows Practice â&#x20AC;&#x201C; Context bonds currently at this time.

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(No Author) Definition of Substituent (oxford online dictionary) http://oxforddictionaries.com/definition/english/substituent?q=substituents [Accessed 28th February 2013]

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(No Author) Dry Ice safety (Commercial Dry Ice supplier) http://www.dryiceuk.com/safety [Accessed 18th March 2013]

(No Author) The Plinth Rejected: Minimalism (Online Arts Blog) http://www.fringeartsbath.co.uk/plinth-by-plinth/ [Accessed 4th March 2013]

Berger, John, Ways of Seeing, (London: British Broadcasting Corporation and Penguin Books, 1972)

Bishop, Claire, Artificial Hells: Participatory art and the politics of spectatorship, (London: Verso, 2012)

Bishop, Claire ‘Art of the Encounter: Antagonism and Relational Aesthetics’, Circa, No. 114 (Winter, 2005), pp. 32-35

Bishop, Claire, ‘Participation’ Documents from Contemporary Art, (London: The Whitechapel Gallery, 2006)

Cohen, Seth Kim, ‘The Artist’s Body as Gravity Makes Itself Its Master’ Open Systems Symposium, Tate Modern, London, (2005 < http://www.kim-

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cohen.com/Assets/Texts/Kim-Cohen_Bas%20Jan%20Ader%20(2005).pdf > [Accessed 28th February 2013]

‘Destiny’ Wonders of the Universe, BBC 2, 6th March 2011

Dezeuze, Anna, ‘Tactile Dematerialization, Sensory Politics: Hélio Oiticica's Parangolés’, Art Journal, Vol. 63, No. 2 (Summer, 2004), pp. 58-71

Engel, Robert, Cohen, Jamie Lee L, The Synthesis of Carbon Phosphorous Bonds, 2nd Edition, (Boca ration, London, New York, Washington, D.C.: CRC press LLC 2004)

Henderson, Linda Dalrymple ‘Space, Time, and the Fourth Dimension in 1913 and Beyond1913:’ The Shape of Time talks series, 23rd January 2013 6pm

Laporte, Paul M, ‘Cubism and Science’, The Journal of aesthetics and Art Criticism, Vol 7, No.3 (Mars.1949), pp.243-256

Le Feuvre, Lisa, ‘Failure’, Documents from Contemporary Art, (London: The Whitechapel Gallery, 2010)

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Le Feuvre, Lisa, “Karl Popper, Unended Quest//1974, Experimentation and progress” ‘Failure’, Documents from Contemporary Art, (London: The Whitechapel Gallery, 2010)

Maholy –Nagy, Laszlo, Vision in Motion, (Chicago: Paul Theobald & Co, June 1947)

McCall, Anthony; artist's talk, Tate Liverpool Auditorium, Saturday 17 November 2012, 14.00 – 15.00

McEwen, William E, Berlin, Darrell K, Organophosphorus stereochemistry Part Two P (V) Compounds, (Stroudsburg, Pa: Dowden, Hutchinson & Ross; [New York]: distributed by Halsted Press, 1975)

McHiggins, Sophie Helena Martha, ‘The VLD (Very Large Dissertation): a critical essay on the shared role of the artist and scientist as creator, and the subsequent overlap between their two respective practices’, (Unpublished Bachelor Thesis, The University of Leeds 2012)

O’Doherty, Brian Inside the white cube: the ideology of the gallery space (Berkeley, Calif.; London: University of California Press, 1999)

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Private correspondence via email between Dr. Neil Thomas and myself, teacher at The University of Leeds, School of Physics and astronomy. Permission granted.

Private correspondence via email between Mr. Pete Morton and myself, Studio and Exhibitions technician The University of Leeds, Fine Art, History of Art and Cultural studies. Permission granted.

Silva, Corinne; Artists Talk, The university of Leeds, 20th February 2013

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Practice In Context