1-Phenyl-1,2-propanedione [C9H8O2]

1-Phenyl-1,2-propanedione [C9H8O2]

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182 reactions in Reaxys

2018-08-07 13h:38m:45s (UTC)

O

1. Query

O

Search as: Product, As drawn, No mixtures ) AND (IDE.RN='579-07-7') AND (IDE.INCHI='BVQVLAIMHVDZEL-UHFFFAOYSA-N') NOT (RX.RXRN=878450))

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1-Phenyl-1,2-propanedione [C9H8O2]

O

O

Rx-ID: 1548764 View in Reaxys 1/182 Yield 100 %

Conditions & References With sodium periodate, sulfuric acid, C31H29Br2N3Ru*CH2Cl2 in water, acetonitrile, Time= 0.5h, T= 25 °C , Inert atmosphere, Schlenk technique Daw, Prosenjit; Petakamsetty, Ramu; Sarbajna, Abir; Laha, Siladitya; Ramapanicker, Ramesh; Bera, Jitendra K.; Journal of the American Chemical Society; vol. 136; nb. 40; (2014); p. 13987 - 13990 View in Reaxys

100 %

Typical method for isolation of aldehydes and diketone General procedure: The typical solution containing 1 mmol of substrates, 0.1 mol percent RuCl3 and 3 equiv of PhI(OAc)2, was heated and kept at constant 30°C. After Reaction for a period of time, the mixture was then separated with separatory funnel and the dichloromethane phase was dried over anhydrous Na2SO4, filtered and the solvent removed under vacuum. The crude product was purified via a standard silica gel chromatography using hexanes/ethyl acetate as eluent to give the desired aldehyde and diketone products. The isolated products were characterized by NMR (in CDCl3 with TMS as an internal standard) and ESI-MS. All the reactions were performed at least three times to establish there producibility and reliability.

With ruthenium trichloride, [bis(acetoxy)iodo]benzene in dichloromethane, water, Time= 1.5h, T= 30 °C Mi, Chun; Li, Lu; Meng, Xiang-Guang; Yang, Ren-Qiang; Liao, Xiao-Hong; Tetrahedron; vol. 72; nb. 42; (2016); p. 6705 6710 View in Reaxys

98.8 %

2 :Under room temperature into thereaction kettle add 1mmol of formula compound (I) and 15ml ofAcetone, then gain slowly added 2.5mmol of Mercury acetate and 2.5mmol ofwater, then while stirring the reaction drop wise added 62mg offerrocene mass ratio as 0.25: 0.25: 1 , Additive mixture of Salicylic acidand triethyloxonium tetrafluoroborate, after mixing continue to stir thereaction for 1.5h, through by TLC Monitoredreaction end point after the completion of the reaction system was added toan equal volume of water then using ethyl acetate three times extra. Combined organicphase, add 1/2 machine phase volume ofsaturated salt water washing, separateorganic phase after adding anhydrous sodium sulfate dry and finallythe actual Organic solvent wasremoved by vacuum distillation and the residue was purified by silica gelcolumn chromatography, to obtain the compound of formula (II), a yield of 98.8percent.Purity99. 3percent (HPLC).

With ferrocene, mercury(II) diacetate, water, triethyloxonium fluoroborate, salicylic acid in acetone, Time= 1.5h, T= 20 °C , Reagent/catalyst, Solvent Patent; WEI, JIANHUA; (9 pag.); CN103936540; (2016); (B) Chinese View in Reaxys

97 %

With [1,4,7-Me3-1,4,7-triazacyclononane(CF3CO2)RuIVO2]ClO4, trifluoroacetic acid in acetonitrile, Time= 5h, T= 20 °C Che; Yu; Chan; Cheng; Peng; Lau; Li; Journal of the American Chemical Society; vol. 122; nb. 46; (2000); p. 11380 - 11392 View in Reaxys

94 %

Representative procedure for the conversion of internal alkynes to 1,2-diketones: General procedure: To a solution of 1,2-diphenylethyne (5a) (500mg, 2.808mmol) in 1,4-dioxane, water (20mL:5mL v/v), complex 3a (63mg, 0.112mmol, 4molpercent), AgNO3 (38mg, 0.224mmol, 8molpercent) were added and the reaction mixture was stirred at 90°C, the progress of the reaction was monitored by TLC. After 19h the reaction mixture was cooled to room temperature, diluted with water and extracted with CH2Cl2. The separated organic layer was dried over Na2SO4, concentrated under vacuum. The residue was subjected to silica gel column chromatography by using hexane/EtOAc (9:1, v/v) as eluent to give benzil (6a) (551mg, 2.623mmol) as a yellow solid in 93percent yield. Similarly to a solution of 5b (1000mg, 4.48mmol) in 1,4-dioxane, water (40mL:10mL v/v), complex 3a (102mg, 0.179mmol, 61mg, 4molpercent), AgNO3 (61mg, 0.358mmol, 8molpercent) were added and the reaction mixture was stirred at 90°Cfor 28h to give 6b (871mg, 3.415mmol) as a yellow solid in 76percent yield.

The characterization data for all the 1,2-diketones (6a-l) are given in the supporting information With C25H21ClN5Pd(1+)*Cl(1-), silver nitrate in 1,4-dioxane, water, Time= 14h, T= 90 °C Shaik, Jeelani Basha; Ramkumar, Venkatachalam; Sankararaman, Sethuraman; Journal of Organometallic Chemistry; vol.

860; (2018); p. 1 - 8

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1-Phenyl-1,2-propanedione [C9H8O2]

View in Reaxys 80 %

With ruthenium(IV) oxide, sodium periodate in tetrachloromethane, water, acetonitrile, Time= 1h, Ambient temperature Zibuck, Regina; Seebach, Dieter; Helvetica Chimica Acta; vol. 71; (1988); p. 237 - 240 View in Reaxys

78 %

With mercuric(II) nitrate monohydrate in N,N-dimethyl-formamide, Time= 1h, T= 22 °C Jung, Michael E.; Deng, Gang; Organic Letters; vol. 16; nb. 8; (2014); p. 2142 - 2145 View in Reaxys

75 %

With ammonium peroxydisulfate, diphenyl diselenide in water, acetonitrile, Time= 24h, T= 60 °C Santoro, Stefano; Battistelli, Benedetta; Gjoka, Blerina; Si, Chun-Wing Steven; Testaferri, Lorenzo; Tiecco, Marcello; Santi, Claudio; Synlett; nb. 9; (2010); p. 1402 - 1406 View in Reaxys

75 %

With diphenyl diselenide, water, bis-[(trifluoroacetoxy)iodo]benzene in tetrahydrofuran, Time= 14h, T= 40 °C Tingoli, Marco; Mazzella, Mauro; Panunzi, Barbara; Tuzi, Angela; European Journal of Organic Chemistry; nb. 2; (2011); p. 399 - 404 View in Reaxys

69 %

2. Typical Experimental Procedure for the 1,2-Diketonization of Alkynes 1 or 3 General procedure: 1 or 3 (0.2 mmol), Cu(0) powder (0.64 mg, 5 mopercent), Selectfluor (141.7 mg, 0.4 mmol, 2equiv), and CH3CN:H2O = 50:1 (V/V, 2 mL) were added to a 10-mL flask. Then the reaction mixture was stirred at room temperature for given times (see Table 2). Upon completion, the resulting mixture was diluted with CH2Cl2 (10 mL) and filtered through Celite.

After evaporation of the solvent under vacuum, the residue was purified by column chromatography on silica gel (100-200 mesh) using petroleum ether-EtOAc (20/1−3/1) as eluent to give pure 2 or 4.

With water, copper, Selectfluor in acetonitrile, Time= 4h, T= 20 °C Zhang, Wenxia; Zhang, Jian; Liu, Yunkui; Xu, Zhenyuan; Synlett; vol. 24; nb. 20; (2013); p. 2709 - 2714; Art.No: ST-2013W0765-L View in Reaxys

67 %

With palladium dichloride in dimethyl sulfoxide, Time= 3h, T= 115 °C Yusubov, M. S.; Chi, Ki Whan; Krasnokutskaya, E. A.; Vasil'eva, V. P.; Filimonov, V. D.; Russian Journal of Organic Chemistry; vol. 31; nb. 11; (1995); p. 1503 - 1506; Zhurnal Organicheskoi Khimii; vol. 31; nb. 11; (1995); p. 1675 - 1678 View in Reaxys

67 %

With sodium periodate, C54H45ClN9Ru2 (3+)*2Cl(1-)*Br(1-) in water, acetone, T= 20 °C , Catalytic behavior, Reagent/catalyst Gupta, Suraj K.; Choudhury, Joyanta; Chemical Communications; vol. 52; nb. 16; (2016); p. 3384 - 3387 View in Reaxys

51 %

With sodium periodate, C23H24ClN4Ru(1+)*Br(1-) in water, acetone, T= 20 °C , Catalytic behavior, Reagent/catalyst Gupta, Suraj K.; Sahoo, Sandeep K.; Choudhury, Joyanta; Organometallics; vol. 35; nb. 15; (2016); p. 2462 - 2466 View in Reaxys

35 %

With [bis(acetoxy)iodo]benzene, copper(II) bis(trifluoromethanesulfonate), acetic acid, Time= 12h, T= 20 °C Xia, Xiao-Feng; Gu, Zhen; Liu, Wentao; Wang, Ningning; Wang, Haijun; Xia, Yongmei; Gao, Haiyan; Liu, Xiang; Organic and Biomolecular Chemistry; vol. 12; nb. 48; (2014); p. 9909 - 9913 View in Reaxys

33 %

4.3. General procedures for oxidation of alkynes General procedure: Alkyne (0.5 mmol), Pd(OAc)2 (10 mol percent), and CuBr2 (10 mol percent) were added to DMSO (2.0 mL) in an oven-dried flask under air. The reaction mixture was heated in an oil bath at designated temperature for 20 h. After the reaction was complete, 10 mL water was added and the mixture was extracted with ethyl acetate. The combined organic phases were dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by column chromatography (hexane/ethyl acetate) to afford the pure products.

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1-Phenyl-1,2-propanedione [C9H8O2]

With palladium diacetate, dimethyl sulfoxide, copper(ll) bromide, Time= 20h, T= 120 °C Gao, Ang; Yang, Fan; Li, Ji; Wu, Yangjie; Tetrahedron; vol. 68; nb. 25; (2012); p. 4950 - 4954 View in Reaxys 7%

With 18-crown-6 ether, (COCl2)2 in hexane, Time= 2h, T= -15 - -10 °C Nagano, Tetsuo; Yokoohji, Kiyomi; Hirobe, Masaaki; Tetrahedron Letters; vol. 25; nb. 9; (1984); p. 965 - 968 View in Reaxys

65 % Chromat.

With iodosylbenzene, tris(triphenylphosphine)ruthenium(II) chloride in dichloromethane, Time= 0.25h, Ambient temperature Mueller, Paul; Godoy, Jose; Helvetica Chimica Acta; vol. 64; nb. 8; (1981); p. 2531 - 2533 View in Reaxys With dihydrogen peroxide, iron(II) in acetonitrile, Yield given Sugimoto, Hiroshi; Sawyer, Donald T.; Journal of the American Chemical Society; vol. 106; nb. 15; (1984); p. 4283 - 4285 View in Reaxys

33.8 %Chromat.

With C3H7NO*C31H31Cl4Fe2N7O3, dihydrogen peroxide in acetonitrile, Time= 1h, T= 60 °C Khattar, Raghvi; Hundal; Mathur, Pavan; Inorganica Chimica Acta; vol. 390; (2012); p. 129 - 134 View in Reaxys Wacker Oxidation Zhou, Wei; Li, Hongji; Wang, Lei; Organic Letters; vol. 14; nb. 17; (2012); p. 4594 - 4597 View in Reaxys

O

HO

O

O

Rx-ID: 31787576 View in Reaxys 2/182 Yield 75%

Conditions & References With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione, Time= 4h, T= 80 °C Guha, Somraj; Kazi, Imran; Mukherjee, Pranamita; Sekar, Govindasamy; Chemical Communications; vol. 53; nb. 79; (2017); p. 10942 - 10945 View in Reaxys

60 %

2.3. General procedure for oxidation of α-hydroxy ketones General procedure: A mixture of α-hydroxy ketone (0.2 mmol), Fe3O4·MNPs (30 molpercent)and ethanol (1.5 mL) were placed in a sealed tube. The reaction mixturewas heated at 80 °C. After completion of reactions, monitored by thinlayer chromatography, the catalyst was separated magnetically. Thereaction solution was concentrated under reduced pressure and thecrude material was purified by preparative thin-layer chromatographywith petroleum ether-EtOAc as eluent.

With air, magnetic magnetite nanoparticles in ethanol, Time= 9h, T= 80 °C , Sealed tube, Green chemistry Li, Xiaona; Xia, Dandan; Wen, Zhiyong; Gong, Bowen; Sun, Maolin; Wu, Yue; Zhang, Jie; Sun, Jun; Wu, Yang; Bao, Kai; Zhang, Weige; Molecular Catalysis; vol. 454; (2018); p. 63 - 69 View in Reaxys

49 %

With oxygen in acetonitrile, Time= 10h, T= 100 °C , p= 750.075Torr , Irradiation, Autoclave, Green chemistry, Catalytic behavior Zheng, Zhishuo; Zhou, Xiaosong; Chinese Journal of Chemistry; vol. 30; nb. 8; (2012); p. 1683 - 1686,4 View in Reaxys

38 %

4.2. General procedure for the oxidation General procedure: A mixture of a substrate (0.6 mmol), vinyl bromide 2a (0.06 mmol) in DMSO (1.1 mL) was heated in an open flask (the temperature of an oil bath and the reaction time are specified in refPreviewPlaceHolderTable 2). After the completion of the reaction (checked by TLC), the reaction mixture was diluted with water (11 mL), saturated with NaCl and extracted with ethyl acetate (5.x.4 mL). Only in the case of the synthesis of arylglyoxals the organic layer was additionally washed

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1-Phenyl-1,2-propanedione [C9H8O2]

with Na2CO3 (0.12 mmol in 2 mL of water), with saturated aq NaCl and dried with anhydrous Na2SO4. Column chromatography (eluent: gradient petrolether/ethyl acetate) of the extract gave the pure products.

With (Z/E)-2-bromo-2-[4-oxothiazolidin-2-ylidene]-N-phenylacetamide, dimethyl sulfoxide, Time= 2h, Reflux Baranac-Stojanovic, Marija; Markovic, Rade; Stojanovic, Milovan; Tetrahedron; vol. 67; nb. 41; (2011); p. 8000 - 8008 View in Reaxys 25 %Chromat.

4.5.5. Aerobic oxidation of 2-hydroxy-1-phenylpropan-1-one catalyzedby PI-Au 4l.

General procedure: 4.5.5. Aerobic oxidation of 2-hydroxy-1-phenylpropan-1-one catalyzedby PI-Au 4l. 2-Hydroxy-1-phenylpropan-1-one (5a) (37.5 mg, 0.25 mmol), PI-Au 4l (0.240 mmol/g, 1 mol percent), toluene (1.0 mL), and water (1.0 mL) were combined in a round-bottom flask. The mixture was stirred for 12 h under O2 at 80 °C. The catalyst was collected by filtration and washed with ethyl acetate, using a Kiriyamarohto funnel. The aqueous layer was extracted with ethyl acetate (20-30 mL). The combined organic layers were dried over sodium sulfate. The yield was determined by GC analysis with reference to an internal standard (anisole).

With oxygen in water, toluene, Time= 12h, T= 80 °C Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys

N

O N

O O

Rx-ID: 47301139 View in Reaxys 3/182 Yield

Conditions & References

92 %

With 2,6-dichloropyridine N-oxide in dichloromethane, Time= 0.166667h, T= 20 °C , Molecular sieve, Inert atmosphere Yu, Yang; Sha, Qiang; Cui, Hui; Chandler, Kory S.; Doyle, Michael P.; Organic Letters; vol. 20; nb. 3; (2018); p. 776 - 779 View in Reaxys O

O N HO

O

Rx-ID: 669770 View in Reaxys 4/182 Yield 94 %

Conditions & References With water, Dess-Martin periodane in dichloromethane, Time= 0.333333h, Ambient temperature Chaudhari, Sachin S.; Akamanchi, Krishnacharya G.; Synthesis; nb. 5; (1999); p. 760 - 764 View in Reaxys

88 %

With 2,6-dicarboxypyridinium chlorochromate in acetonitrile, Time= 0.316667h, T= 20 °C Hosseinzadeh, Rahman; Tajbakhsh, Mahmood; Niaki, Mohammad Yazdani; Tetrahedron Letters; vol. 43; nb. 51; (2002); p.

9413 - 9416 View in Reaxys

85 %

With 2,6-dicarboxypyridinium fluorochromate, Time= 0.5h Tajbakhsh, Mahmood; Hosseinzadeh, Rahman; Ramzanian-Lahmali, Farhad; Sadatshahabi, Marzieh; Journal of the Chinese Chemical Society; vol. 52; nb. 5; (2005); p. 1005 - 1009 View in Reaxys

80 %

With chromium(VI) oxide, silica gel in toluene, Time= 4h, T= 72 - 75 °C , Oxidation, Deoximation Bendale, Pravin M.; Khadilkar, Bhushan M.; Synthetic Communications; vol. 30; nb. 4; (2000); p. 665 - 669 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

75 %

With manganese(IV) oxide, silica gel, Time= 0.1h, microwave irradiation Khadilkar, Bhushan M.; Madyar, Virendra R.; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 41; nb. 5; (2002); p. 1081 - 1082 View in Reaxys

74.9 %

2.2 :(2) In a 1000 liter reactor,Add 200 kg of hydrochloric acid,200 kg of formaldehyde aqueous solution and 220 kg of ethanol,Under cooling with ice water, 200 kg of l-phenyl 1,2-propanedione-2-oxime was added in portions at a temperature of 15 ° C,The addition process is an exothermic reaction,After stirring, the reaction was stirred at room temperature for 20 hours,Extracted with 400 kg of dichloromethane,And then washed with saturated sodium bicarbonate solution and water once,Removal of methylene chloride to obtain crude product,Distillation under reduced pressure to obtain yellow liquid 136kg,The yield was 74.9percent.

With hydrogenchloride, formaldehyd in ethanol, water, Time= 20h, T= 15 - 20 °C , Cooling with ice, Large scale Patent; Huaihua Jinxin New Materials Co., Ltd.; Wang Youming; (5 pag.); CN106883109; (2017); (A) Chinese View in Reaxys With sulfuric acid v. Pechmann; Mueller; Chemische Berichte; vol. 21; (1888); p. 2119 View in Reaxys Mueller; v. Pechmann; Chemische Berichte; vol. 22; (1889); p. 2129 View in Reaxys With isopentyl nitrite Manasse; Chemische Berichte; vol. 21; (1888); p. 2177 View in Reaxys With hydrogenchloride, formaldehyd, T= 20 °C Amitina; Grigor'ev; Tikhonov; Russian Chemical Bulletin; vol. 55; nb. 6; (2006); p. 1046 - 1051 View in Reaxys O

O

O

O

Rx-ID: 35856680 View in Reaxys 5/182 Yield

Conditions & References

90 %

With aluminum (III) chloride, Oxone in water, Time= 1h, T= 20 °C Stergiou, Anastasios; Bariotaki, Anna; Kalaitzakis, Dimitris; Smonou, Ioulia; Journal of Organic Chemistry; vol. 78; nb.

14; (2013); p. 7268 - 7273 View in Reaxys

85 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, acetic acid, copper(I) bromide, Time= 2h, T= 100 °C Zhou, Peng-Jun; Li, Cheng-Kun; Zhou, Shao-Fang; Shoberu, Adedamola; Zou, Jian-Ping; Organic and Biomolecular Chemistry; vol. 15; nb. 12; (2017); p. 2629 - 2637 View in Reaxys O HO

O

Rx-ID: 39395148 View in Reaxys 6/182 Yield

Conditions & References Reaction Steps: 2 1.1: N-Bromosuccinimide / 1,4-dioxane 1.2: 24 h / 20 °C

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1-Phenyl-1,2-propanedione [C9H8O2]

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C With N-Bromosuccinimide, 3-chloro-benzenecarboperoxoic acid in 1,4-dioxane, dichloromethane Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb.

3; (2015); p. 406 - 409 View in Reaxys Reaction Steps: 3 1: N-Bromosuccinimide / 1,4-dioxane / 1 h 2: 1,4-dioxane 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C With N-Bromosuccinimide, 3-chloro-benzenecarboperoxoic acid in 1,4-dioxane, dichloromethane Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb.

3; (2015); p. 406 - 409 View in Reaxys Reaction Steps: 2 1.1: iodine; acetone / 1,4-dioxane / 0.08 h / 20 °C 1.2: 24 h / 80 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 4 h / 80 °C With iodine, acetone, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in 1,4-dioxane Guha, Somraj; Kazi, Imran; Mukherjee, Pranamita; Sekar, Govindasamy; Chemical Communications; vol. 53; nb. 79; (2017); p. 10942 - 10945 View in Reaxys O

Br

O

Rx-ID: 39395181 View in Reaxys 7/182 Yield

Conditions & References Reaction Steps: 3 1.1: magnesium; iodine / tetrahydrofuran / 0.5 h / Inert atmosphere 1.2: 0 °C / Inert atmosphere 2.1: N-Bromosuccinimide / 1,4-dioxane 2.2: 24 h / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C With N-Bromosuccinimide, iodine, magnesium, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, 1,4-dioxane, dichloromethane, 1.1: |Grignard Reaction Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb.

3; (2015); p. 406 - 409 View in Reaxys Reaction Steps: 4 1.1: magnesium; iodine / tetrahydrofuran / 0.5 h / Inert atmosphere 1.2: 0 °C / Inert atmosphere 2.1: N-Bromosuccinimide / 1,4-dioxane / 1 h 3.1: 1,4-dioxane 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C With N-Bromosuccinimide, iodine, magnesium, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, 1,4-dioxane, dichloromethane, 1.1: |Grignard Reaction Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb.

3; (2015); p. 406 - 409 View in Reaxys Reaction Steps: 3 1.1: magnesium; iodine / tetrahydrofuran / 0.5 h / Inert atmosphere 1.2: 0 °C / Inert atmosphere 2.1: iodine; acetone / 1,4-dioxane / 0.08 h / 20 °C

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1-Phenyl-1,2-propanedione [C9H8O2]

2.2: 24 h / 80 °C 3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 4 h / 80 °C With iodine, magnesium, acetone, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, 1,4-dioxane Guha, Somraj; Kazi, Imran; Mukherjee, Pranamita; Sekar, Govindasamy; Chemical Communications; vol. 53; nb. 79; (2017); p. 10942 - 10945 View in Reaxys

Si

Si Cl

O

O

Si Si

Cl

Cl Cl Sn

Sn

O Si

Si

Si Si

O

Rx-ID: 46298102 View in Reaxys 8/182 Yield

Conditions & References

95 %, 89 %

in hexane, Time= 12h, T= 20 °C , Schlenk technique, Inert atmosphere Lu, Qiong; Yan, Chenting; Xiao, Xu-Qiong; Li, Zhifang; Wei, Ningka; Lai, Guoqiao; Kira, Mitsuo; Organometallics; vol.

36; nb. 18; (2017); p. 3633 - 3637 View in Reaxys O

O

O Cl

Rx-ID: 46298106 View in Reaxys 9/182 Yield

Conditions & References Reaction Steps: 2 1: hexane / 20 °C / Inert atmosphere; Schlenk technique 2: hexane / 12 h / 20 °C / Schlenk technique; Inert atmosphere in hexane Lu, Qiong; Yan, Chenting; Xiao, Xu-Qiong; Li, Zhifang; Wei, Ningka; Lai, Guoqiao; Kira, Mitsuo; Organometallics; vol.

36; nb. 18; (2017); p. 3633 - 3637 View in Reaxys O O

O

Rx-ID: 724581 View in Reaxys 10/182 Yield 86%

Conditions & References 1.A : STEP A: STEP A: 1-phenyl-propane-1,2-dione 6.0 kg (44.78 moles) of propiophenone and 92 g of anhydrous aluminum chloride were added to 6 liters of ether followed by 17.2 kg (107.5 mole) of bromine at a rate to maintained a gentle reflux.

When the addition was complete (approximately 6 hours), the mixture was heated to reflux overnight and then the solvent was removed under vacuum to obtain a lachrymatory dark red/orange oil.

The oil was slowly added to a solution of 2.81 kg (122.2 mmole)of sodium in 45 l of methanol while maintaining the temperature below 20° C. When the addition was complete, 12.5 liters of concentrated hydrochloric acid were added and the mixture was stirred at room temperature for 1 hour.

The precipitate was filtered off and the filtrate reduced in volume to approximately 25 liters by distillation of the methanol.

The residue was partitioned between 10 liters of chloroform and 10 liters of water.

Then, the organic phase was separated and the aqueous phase extracted twice with 5 liters of chloroform.

The combined chloroform solutions were dried over sodium sulfate and evaporated to dryness.

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1-Phenyl-1,2-propanedione [C9H8O2]

The residue was fractionally distilled under vacuum through a 30 cm Fenske column to obtain 5.7 kg of 1-phenylpropane-1,2dione (86percent yield) and a boiling point of 77°-85° C. at 1-2 mm Hg. With hydrogenchloride, bromine, sodium, aluminium trichloride in methanol, chloroform, water Patent; Tully; Wilfred R.; US4643999; (1987); (A) English View in Reaxys 83 %

Stage 1: With [hydroxy(p-nitrobenezenesulfonyloxy)iodo]benzene, Time= 0.025h, microwave irradiation Stage 2: With pyridine N-oxide, Time= 0.00833333h, microwave irradiation Lee, Jong Chan; Park, Hong-Jun; Park, Jin Young; Tetrahedron Letters; vol. 43; nb. 32; (2002); p. 5661 - 5664 View in Reaxys

46 %

4.2. General procedure for the oxidation General procedure: A mixture of a substrate (0.6 mmol), vinyl bromide 2a (0.06 mmol) in DMSO (1.1 mL) was heated in an open flask (the temperature of an oil bath and the reaction time are specified in refPreviewPlaceHolderTable 2). After the completion of the reaction (checked by TLC), the reaction mixture was diluted with water (11 mL), saturated with NaCl and extracted with ethyl acetate (5.x.4 mL). Only in the case of the synthesis of arylglyoxals the organic layer was additionally washed with Na2CO3 (0.12 mmol in 2 mL of water), with saturated aq NaCl and dried with anhydrous Na2SO4. Column chromatography (eluent: gradient petrolether/ethyl acetate) of the extract gave the pure products.

With (Z/E)-2-bromo-2-[4-oxothiazolidin-2-ylidene]-N-phenylacetamide, dimethyl sulfoxide, Time= 24h, Reflux Baranac-Stojanovic, Marija; Markovic, Rade; Stojanovic, Milovan; Tetrahedron; vol. 67; nb. 41; (2011); p. 8000 - 8008 View in Reaxys With selenium(IV) oxide, ethanol Riley; Morley; Friend; Journal of the Chemical Society; (1932); p. 1875,1880 View in Reaxys With hydrogenchloride, dinitrogen tetraoxide, calcium chloride, T= 60 °C Coles; Manske; Johnson; Journal of the American Chemical Society; vol. 51; (1929); p. 2271 View in Reaxys With hydrogenchloride, methanol, aluminium trichloride, bromine, sodium, Yield given. Multistep reaction Danswan, Geoffrey; Kennewell, Peter D.; Tully, W. Roger; Journal of Heterocyclic Chemistry; vol. 26; (1989); p. 293 - 299 View in Reaxys With hydrogen cyanide, sulfuric acid, Yield given. Multistep reaction Rao, T. S. S.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 329; nb. 3; (1987); p. 474 - 482 View in Reaxys Reaction Steps: 2 1: conc. HCl; n-butyl nitrite / methanol / 14 h / 20 °C 2: conc. HCl; aq. formaldehyde / 20 °C With hydrogenchloride, formaldehyd, n-Butyl nitrite in methanol Amitina; Grigor'ev; Tikhonov; Russian Chemical Bulletin; vol. 55; nb. 6; (2006); p. 1046 - 1051 View in Reaxys With selenium(IV) oxide, water in isopropyl alcohol, Reflux Bardasov; Kayukova; Kayukov; Ershov; Nasakin; Russian Journal of Applied Chemistry; vol. 82; nb. 8; (2009); p. 1431 1434 View in Reaxys Stage 1: With [hydroxy(p-nitrobenezenesulfonyloxy)iodo]benzene in acetonitrile, Time= 1h, Reflux Stage 2: With pyridine N-oxide in toluene, Time= 2h, Reflux Sun, Tian; Zhang, Xumu; Advanced Synthesis and Catalysis; vol. 354; nb. 17; (2012); p. 3211 - 3215 View in Reaxys

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With iodine, dimethyl sulfoxide, T= 100 °C Viswanadham, K. K. Durga Rao; Prathap Reddy, Muktapuram; Sathyanarayana, Pochampalli; Ravi, Owk; Kant, Ruchir; Bathula, Surendar Reddy; Chemical Communications; vol. 50; nb. 88; (2014); p. 13517 - 13520 View in Reaxys Reaction Steps: 3 1: bromine / 1 h 2: 1,4-dioxane 3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C With bromine, 3-chloro-benzenecarboperoxoic acid in 1,4-dioxane, dichloromethane Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb.

3; (2015); p. 406 - 409 View in Reaxys Reaction Steps: 2 1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 0 °C 2: oxygen / N,N-dimethyl-formamide / 12 h / 80 °C / 760.05 Torr With n-butyllithium, oxygen, diisopropylamine in tetrahydrofuran, hexane, N,N-dimethyl-formamide Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys Reaction Steps: 2 1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 0 °C 2: oxygen / toluene; water / 16 h / 100 °C / 760.05 Torr With n-butyllithium, oxygen, diisopropylamine in tetrahydrofuran, hexane, water, toluene Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys Reaction Steps: 3 1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 0 °C 2: oxygen / toluene; water / 15 h / 60 °C / 760.05 Torr 3: oxygen / toluene; water / 12 h / 80 °C With n-butyllithium, oxygen, diisopropylamine in tetrahydrofuran, hexane, water, toluene Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys Reaction Steps: 3 1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 0 °C 2: oxygen / toluene; water / 16 h / 100 °C / 760.05 Torr 3: oxygen / toluene; water / 12 h / 80 °C With n-butyllithium, oxygen, diisopropylamine in tetrahydrofuran, hexane, water, toluene Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys Reaction Steps: 4 1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 0 °C 2: oxygen / toluene / 15 h / 80 °C / 760.05 Torr 3: 2,2'-azobis(isobutyronitrile) / toluene; water / 13 h / 80 °C 4: oxygen / toluene; water / 12 h / 80 °C With n-butyllithium, 2,2'-azobis(isobutyronitrile), oxygen, diisopropylamine in tetrahydrofuran, hexane, water, toluene Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys Reaction Steps: 4 1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - 0 °C 2: oxygen / toluene; water / 15 h / 60 °C / 760.05 Torr 3: 2,2'-azobis(isobutyronitrile) / toluene; water / 13 h / 80 °C 4: oxygen / toluene; water / 12 h / 80 °C

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With n-butyllithium, 2,2'-azobis(isobutyronitrile), oxygen, diisopropylamine in tetrahydrofuran, hexane, water, toluene Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys Reaction Steps: 2 1: dihydrogen peroxide; sodium nitrite; iodine / dimethyl sulfoxide; water / 8 h / 100 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 72 h / 60 °C With dihydrogen peroxide, iodine, 1,8-diazabicyclo[5.4.0]undec-7-ene, sodium nitrite in water, dimethyl sulfoxide, acetonitrile Dighe, Shashikant U.; Mukhopadhyay, Sushobhan; Priyanka, Kumari; Batra, Sanjay; Organic Letters; vol. 18; nb. 17; (2016); p. 4190 - 4193 View in Reaxys With selenium(IV) oxide in 1,4-dioxane Fedoseev; Belikov, M. Yu.; Ershov; Bardasov; Tafeenko; Russian Journal of Organic Chemistry; vol. 52; nb. 10; (2016); p.

1440 - 1443; Zh. Org. Khim.; vol. 52; nb. 10; (2016); p. 1450 - 1453,4 View in Reaxys HO

O

O

N

O

O

Rx-ID: 41758361 View in Reaxys 11/182 Yield

Conditions & References With aluminum (III) chloride, sodium nitrite in N,N-dimethyl-formamide, Time= 1.5h, T= 90 °C , Schlenk technique Ge, Jing-Jie; Yao, Chuan-Zhi; Wang, Mei-Mei; Zheng, Hong-Xing; Kang, Yan-Biao; Li, Yadong; Organic Letters; vol. 18; nb. 2; (2016); p. 228 - 231 View in Reaxys

O

O HO

H

O

Rx-ID: 42526326 View in Reaxys 12/182 Yield

Conditions & References With dichlorobis(dimethylsulfoxide)dioxomolybdenum(VI), dimethyl sulfoxide, Time= 0.166667h, T= 90 °C , Sealed tube, Microwave irradiation, Green chemistry, chemoselective reaction García, Nuria; Rubio-Presa, Rubén; García-García, Patricia; Fernández-Rodríguez, Manuel A.; Pedrosa, María R.; Arnáiz, Francisco J.; Sanz, Roberto; Green Chemistry; vol. 18; nb. 8; (2016); p. 2335 - 2340 View in Reaxys

> 98 %Spectr.

With oxygen, potassium carbonate in water, Time= 36h, T= 80 °C , Green chemistry Yu, Yangyang; Lin, Chenlu; Li, Bing; Zhao, Pengxiang; Zhang, Shiyong; Green Chemistry; vol. 18; nb. 12; (2016); p. 3647 - 3655 View in Reaxys O

O O N

O

O

Rx-ID: 43196209 View in Reaxys 13/182

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Yield

Conditions & References

65 %

With 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile, Time= 72h, T= 60 °C Dighe, Shashikant U.; Mukhopadhyay, Sushobhan; Priyanka, Kumari; Batra, Sanjay; Organic Letters; vol. 18; nb. 17; (2016); p. 4190 - 4193 View in Reaxys

O

O

Br

O

Rx-ID: 22064589 View in Reaxys 14/182 Yield

Conditions & References Reaction Steps: 2 1: AgNO3 2: piperidine; diethyl ether With piperidine, diethyl ether, silver nitrate Emmons; Freeman; Journal of the American Chemical Society; vol. 77; (1955); p. 4415 View in Reaxys Reaction Steps: 2 1: 1,4-dioxane 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C With 3-chloro-benzenecarboperoxoic acid in 1,4-dioxane, dichloromethane Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb.

3; (2015); p. 406 - 409 View in Reaxys

O

O

O

N O

Rx-ID: 39395202 View in Reaxys 15/182 Yield

Conditions & References With 3-chloro-benzenecarboperoxoic acid in dichloromethane, Time= 12h, T= 20 °C Guha, Somraj; Rajeshkumar, Venkatachalam; Kotha, Surya Srinivas; Sekar, Govindasamy; Organic Letters; vol. 17; nb.

3; (2015); p. 406 - 409 View in Reaxys O

O N

O

O

O O

Rx-ID: 40187498 View in Reaxys 16/182 Yield 91 %

Conditions & References With triethylamine, Time= 16h, T= 90 °C , Inert atmosphere Andia, Alexander A.; Miner, Matthew R.; Woerpel; Organic Letters; vol. 17; nb. 11; (2015); p. 2704 - 2707

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View in Reaxys O

O

Rx-ID: 40187516 View in Reaxys 17/182 Yield

Conditions & References Reaction Steps: 2 1: oxygen; tetrakis(acetonitrile)copper(I) perchlorate / acetonitrile / 18 h 2: triethylamine / 16 h / 90 °C / Inert atmosphere With tetrakis(acetonitrile)copper(I) perchlorate, oxygen, triethylamine in acetonitrile Andia, Alexander A.; Miner, Matthew R.; Woerpel; Organic Letters; vol. 17; nb. 11; (2015); p. 2704 - 2707 View in Reaxys O O

O

Rx-ID: 40639530 View in Reaxys 18/182 Yield

Conditions & References With tert.-butylhydroperoxide, C20H16CuN4O4, sodium acetate, cetyltrimethylammonim bromide in acetonitrile, Time= 10h, T= 35 - 40 °C Kumar, Ravinder; Mathur, Pavan; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 136; nb.

PB; (2015); p. 818 - 823 View in Reaxys O O

O

O HO

Rx-ID: 40639531 View in Reaxys 19/182 Yield

Conditions & References With tert.-butylhydroperoxide, C20H16CuN4O4, sodium acetate in acetonitrile, Time= 10h, T= 35 - 40 °C , Reagent/catalyst Kumar, Ravinder; Mathur, Pavan; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 136; nb.

PB; (2015); p. 818 - 823 View in Reaxys With tert.-butylhydroperoxide, C20H16CuN4O4 in aq. acetate buffer, Time= 10h, T= 35 - 40 °C , Reagent/catalyst, Solvent Kumar, Ravinder; Mathur, Pavan; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 136; nb.

PB; (2015); p. 818 - 823 View in Reaxys With tert.-butylhydroperoxide, C21H16CuN4OS in acetonitrile, Time= 10h, T= 35 - 40 °C Kumar, Ravinder; Mathur, Pavan; Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy; vol. 136; nb.

PB; (2015); p. 818 - 823 View in Reaxys O

O

O HO

Rx-ID: 41001348 View in Reaxys 20/182

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Yield

Conditions & References

57%

With [bis(acetoxy)iodo]benzene, sulfuric acid in 1,2-dichloro-ethane Liu, Le; Zhang-Negrerie, Daisy; Du, Yunfei; Zhao, Kang; Synthesis (Germany); vol. 47; nb. 19; (2015); p. 2924 - 2930; Art.No: SS-2015-C0218-ST View in Reaxys O

O

O

O

Rx-ID: 41025050 View in Reaxys 21/182 Yield

Conditions & References

63 %

With water, potassium hydrogencarbonate, Selectfluor in acetonitrile, Time= 6h, T= 80 °C , Schlenk technique Wang, Heng; Ren, Shaobo; Zhang, Jian; Zhang, Wei; Liu, Yunkui; Journal of Organic Chemistry; vol. 80; nb. 13; (2015); p.

6856 - 6863 View in Reaxys O O

O

Rx-ID: 41050178 View in Reaxys 22/182 Yield

Conditions & References

20 %, 60 %

With 2,6-dichloropyridine N-oxide, [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate, T= 60 °C , regioselective reaction Chen, Hongyi; Zhang, Liming; Angewandte Chemie - International Edition; vol. 54; nb. 40; (2015); p. 11775 - 11779; Angew.

Chem.; vol. 254; nb. 40; (2015); p. 11775 - 11779,5 View in Reaxys

HO N O

HN

O

O

Rx-ID: 41089409 View in Reaxys 23/182 Yield

Conditions & References With 2C50H56O4P(1-)*Cu(2+) in benzene, T= 60 °C , Molecular sieve Miles, Dillon H.; Guasch, Joan; Toste, F. Dean; Journal of the American Chemical Society; vol. 137; nb. 24; (2015); p. 7632 7635 View in Reaxys

O

O H

O O

Rx-ID: 41726372 View in Reaxys 24/182

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Yield

Conditions & References

43 %

With iron(III) chloride, water, oxygen in dimethyl sulfoxide, Time= 20h, T= 110 °C , p= 760.051Torr , Glovebox, Molecular sieve, Schlenk technique Xing, Qi; Lv, Hui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 52; nb. 3; (2015); p. 489 - 492 View in Reaxys O

O

HO

O

Rx-ID: 38471071 View in Reaxys 25/182 Yield

Conditions & References

80 %

With tetrabutylammonium acetate, palladium diacetate, 8-hydroxyquinoline-2-sulfonic acid in toluene, Time= 6h, T= 100 °C , p= 22502.3Torr Dornan, Laura M.; Clendenning, Grainne M. A.; Pitak, Mateusz B.; Coles, Simon J.; Muldoon, Mark J.; Catalysis Science and Technology; vol. 4; nb. 8; (2014); p. 2526 - 2534 View in Reaxys O

H

O O O

Rx-ID: 38909860 View in Reaxys 26/182 Yield

Conditions & References Stage 1: With potassium cyanide, Schlenk technique, Inert atmosphere, Benzoin Condensation Stage 2:Schlenk technique, Inert atmosphere Takaki, Ken; Ohno, Akira; Hino, Makoto; Shitaoka, Takashi; Komeyama, Kimihiro; Yoshida, Hiroto; Chemical Communications; vol. 50; nb. 82; (2014); p. 12285 - 12288 View in Reaxys O

O O Si

O

Rx-ID: 39684605 View in Reaxys 27/182 Yield

Conditions & References Reaction Steps: 2 1: 2,2'-azobis(isobutyronitrile) / toluene; water / 13 h / 80 °C 2: oxygen / toluene; water / 12 h / 80 °C With 2,2'-azobis(isobutyronitrile), oxygen in water, toluene Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys

Si

O

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O

O

O

O

O Si

O

HO

Rx-ID: 39684611 View in Reaxys 28/182 Yield

Conditions & References

11 %Chro- With oxygen in water, toluene, Time= 15h, T= 60 °C , p= 760.051Torr , Time, Solvent mat., 7 %Chromat., Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 26 %Chro- View in Reaxys mat., 15 %Chromat.

O

O

O

O Si

Si

O

O

Rx-ID: 39684612 View in Reaxys 29/182 Yield

Conditions & References

6 %Chromat., 25 %Chromat., 28 %Chromat.

4.5.4. A typical procedure for aerobic oxidation of silyl enol ethercatalyzed by PI-Au 4l.

General procedure: 4.5.4. A typical procedure for aerobic oxidation of silyl enol ether catalyzed by PI-Au 4l. Trimethyl(1-phenylprop-1-enyloxy)silane (51.5 mg, 0.25 mmol), PI-Au 4l (0.240 mmol/g, 1 mol percent), toluene (1.0 mL), and water (1.0 mL) were combined in a round-bottom flask. The mixture was stirred for 11 h under O2 at 80 °C. After cooling to room temperature, the catalyst was collected by filtration and washed with ethyl acetate, using a Kiriyamarohto funnel. The aqueous layer was extracted with ethyl acetate (20-30 mL). The combined organic layers were dried over sodium sulfate. The yield was determined

by GC analysis with reference to an internal standard (anisole).

With oxygen in water, toluene, Time= 11h, T= 80 °C , p= 760.051Torr , Time, Temperature Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys O

O

O

Si

O

HO

O

Rx-ID: 39684615 View in Reaxys 30/182 Yield

Conditions & References

16 %Chro- With oxygen in water, toluene, Time= 16h, T= 100 °C , p= 760.051Torr , Time, Temperature, Solvent mat., 30 %Chromat., Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 16 %Chro- View in Reaxys mat.

O O

Si

O

O

Rx-ID: 39684616 View in Reaxys 31/182 Yield 27 %Chromat., 12 %Chromat.

Conditions & References With oxygen in N,N-dimethyl-formamide, Time= 12h, T= 80 °C , p= 760.051Torr , Solvent Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys

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O

Si

O

O

Rx-ID: 39684617 View in Reaxys 32/182 Yield

Conditions & References Reaction Steps: 2 1: oxygen / toluene; water / 15 h / 60 °C / 760.05 Torr 2: oxygen / toluene; water / 12 h / 80 °C With oxygen in water, toluene Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys Reaction Steps: 2 1: oxygen / toluene; water / 16 h / 100 °C / 760.05 Torr 2: oxygen / toluene; water / 12 h / 80 °C With oxygen in water, toluene Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys Reaction Steps: 3 1: oxygen / toluene / 15 h / 80 °C / 760.05 Torr 2: 2,2'-azobis(isobutyronitrile) / toluene; water / 13 h / 80 °C 3: oxygen / toluene; water / 12 h / 80 °C With 2,2'-azobis(isobutyronitrile), oxygen in water, toluene Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys Reaction Steps: 3 1: oxygen / toluene; water / 11 h / 80 °C / 760.05 Torr 2: 2,2'-azobis(isobutyronitrile) / toluene; water / 13 h / 80 °C 3: oxygen / toluene; water / 12 h / 80 °C With 2,2'-azobis(isobutyronitrile), oxygen in water, toluene Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys Reaction Steps: 3 1: oxygen / toluene; water / 15 h / 60 °C / 760.05 Torr 2: 2,2'-azobis(isobutyronitrile) / toluene; water / 13 h / 80 °C 3: oxygen / toluene; water / 12 h / 80 °C With 2,2'-azobis(isobutyronitrile), oxygen in water, toluene Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shu; Tetrahedron; vol. 70; nb. 36; (2014); p. 6039 - 6049 View in Reaxys O

O

O

Rx-ID: 780140 View in Reaxys 33/182 Yield 85 %

Conditions & References With pyridine, pyridinium chlorochromate in dichloromethane, Time= 15h, Heating Bonadies, Francesco; Bonini, Carlo; Synthetic Communications; vol. 18; nb. 13; (1988); p. 1573 - 1580 View in Reaxys

82 %

With 2,6-dicarboxypyridinium fluorochromate in acetonitrile, Time= 1h, T= 20 °C

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Sarrafi, Yaghoub; Tajbakhsh, Mahmood; Hosseinzadeh, Rahman; Sadatshahabi, Marzieh; Alimohammadi, Kamal; Synthetic Communications; vol. 42; nb. 5; (2012); p. 678 - 685 View in Reaxys 41 %

With selenium(IV) oxide, Inert atmosphere Schüttler, Christian; Li-Böhmer, Zhen; Harms, Klaus; Von Zezschwitz, Paultheo; Organic Letters; vol. 15; nb. 4; (2013); p.

800 - 803 View in Reaxys With selenium(IV) oxide, diethyl ether Kratzl; Daeubner; Chemische Berichte; vol. 77/79; (1944); p. 519,526 View in Reaxys With 1,4-dioxane, selenium(IV) oxide Wegmann; Dahn; Helvetica Chimica Acta; vol. 29; (1946); p. 1247,1249 View in Reaxys With selenium(IV) oxide Greenfield, Simon; Mackenzie, Kenneth; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1986); p. 1651 - 1666 View in Reaxys General procedure: A stirred solution of deoxybenzoin 1a (196 mg, 1.0 mmol), CuO (88 mg, 1.1 mmol), and iodine (279 mg, 1.1 mmol) was heated at 100 °C for 4 h in DMSO (3 mL), after the disappearance of the starting material (TLC), 1,2-diamine 2a (324 mg, 3.0 mmol) was added and stirred for another 1 h. Then the reaction mixture was poured into 50 mL brine and the aqueous layer was extracted with EtOAc (3×50 mL). The extract was washed with Na2S2O3 solution, dried over anhydrous Na2SO4 then the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether/EtOAc as the eluent to give the expected products 3aa as the yellow solid (240 mg, 85percent yield).

With iodine, dimethyl sulfoxide, copper(II) oxide, Time= 4h, T= 100 °C Lian, Mi; Li, Qi; Zhu, Yanping; Yin, Guodong; Wu, Anxin; Tetrahedron; vol. 68; nb. 47; (2012); p. 9598 - 9605 View in Reaxys O

O O

HO

O O

O

Rx-ID: 37049630 View in Reaxys 34/182 Yield 62 %, 21 %

Conditions & References With iodine, sodium acetate in tetrahydrofuran, water, Time= 3h, T= 35 °C , Irradiation, Green chemistry Miao, Chun-Bao; Wang, Yan-Hong; Xing, Meng-Lei; Lu, Xin-Wei; Sun, Xiao-Qiang; Yang, Hai-Tao; Journal of Organic Chemistry; vol. 78; nb. 22; (2013); p. 11584 - 11589 View in Reaxys O

O

O

O

O

Rx-ID: 33454715 View in Reaxys 35/182 Yield

Conditions & References

29 %Chro- With tert.-butylhydroperoxide, C3H7NO*C31H31Cl4Fe2N7O3 in acetonitrile, Time= 1h, T= 60 °C mat., 27.3 %Chromat., Khattar, Raghvi; Hundal; Mathur, Pavan; Inorganica Chimica Acta; vol. 390; (2012); p. 129 - 134 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

14.4 %Chromat.

O (v1)

N

Cl – (v4)

N

O

N

Pd2+ P (v4)

(v4) C– (v4)

O

(v4)

C–

O

N

(v4) (v4)

P

O

N (v4)(v2)

Pd2+Cl –

(v4)

P Pd2+ C – (v4) (v4) O Cl –

(v2)

(v1)

–Cl Pd2+ P (v4) (v4) – (v4)

C

N

Cl – O O

O

N+

Rx-ID: 34126031 View in Reaxys 36/182 Yield

Conditions & References With water in chloroform-d1, Time= 72h, T= 20 °C , Inert atmosphere, Schlenk technique Meana, Isabel; Albeniz, Ana C.; Espinet, Pablo; Organometallics; vol. 31; nb. 15; (2012); p. 5494 - 5499 View in Reaxys O H

O O

Rx-ID: 31161929 View in Reaxys 37/182 Yield

Conditions & References With silver tetrafluoroborate, (triphenylphosphine)gold(I) chloride, sulfuric acid, water in 1,4-dioxane, Time= 24h, T= 60 °C Cui, Dong-Mei; Zhuang, Dan-Wen; Chen, Ying; Zhang, Chen; Beilstein Journal of Organic Chemistry; vol. 7; (2011); p. 860 - 865 View in Reaxys O

O

O

O

O

O

O O

Rx-ID: 31285383 View in Reaxys 38/182 Yield 60 %, 55 %

Conditions & References With iron(III) chloride, tert.-butylnitrite, Time= 12h, T= 30 °C , Under air, Neat (no solvent) Huang, Lehao; Cheng, Kai; Yao, Bangben; Xie, Yongju; Zhang, Yuhong; Journal of Organic Chemistry; vol. 76; nb. 14; (2011); p. 5732 - 5737 View in Reaxys O O

O N

O

Rx-ID: 31480618 View in Reaxys 39/182 Yield 67 %

Conditions & References With 2,2'-azobis(isobutyronitrile), oxygen, palladium diacetate, sodium carbonate, Time= 20h, T= 120 °C , p= 6080.41Torr , Autoclave

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1-Phenyl-1,2-propanedione [C9H8O2]

Wang, Azhong; Jiang, Huanfeng; Li, Xianwei; Journal of Organic Chemistry; vol. 76; nb. 16; (2011); p. 6958 - 6961 View in Reaxys N

O

O

N O

Rx-ID: 31734704 View in Reaxys 40/182 Yield

Conditions & References Reaction Steps: 2 1: oxygen; sodium hydride / N,N-dimethyl-formamide / 0.2 h / 20 °C 2: hydrogenchloride; formaldehyd; water / ethanol / 0.2 h / 80 °C / Microwave irradiation With hydrogenchloride, formaldehyd, water, oxygen, sodium hydride in ethanol, N,N-dimethyl-formamide Liu, Yu; Yun, Xiliu; Zhang-Negrerie, Daisy; Huang, Jianhui; Du, Yunfei; Zhao, Kang; Synthesis; nb. 18; (2011); p. 2984 2994; Art.No: H55411SS View in Reaxys

N

O

O O

Rx-ID: 31734799 View in Reaxys 41/182 Yield

Conditions & References Reaction Steps: 3 1: sodium acetate / ethanol; water / 2 h 2: oxygen; sodium hydride / N,N-dimethyl-formamide / 0.2 h / 20 °C 3: hydrogenchloride; formaldehyd; water / ethanol / 0.2 h / 80 °C / Microwave irradiation With hydrogenchloride, formaldehyd, water, oxygen, sodium acetate, sodium hydride in ethanol, water, N,N-dimethyl-formamide Liu, Yu; Yun, Xiliu; Zhang-Negrerie, Daisy; Huang, Jianhui; Du, Yunfei; Zhao, Kang; Synthesis; nb. 18; (2011); p. 2984 2994; Art.No: H55411SS View in Reaxys O

O N O

O

Rx-ID: 31734802 View in Reaxys 42/182 Yield

Conditions & References

84 %

With hydrogenchloride, formaldehyd, water in ethanol, Time= 0.2h, T= 80 °C , Microwave irradiation Liu, Yu; Yun, Xiliu; Zhang-Negrerie, Daisy; Huang, Jianhui; Du, Yunfei; Zhao, Kang; Synthesis; nb. 18; (2011); p. 2984 2994; Art.No: H55411SS View in Reaxys

HO

O O

O

HO HO

Rx-ID: 32102838 View in Reaxys 43/182

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1-Phenyl-1,2-propanedione [C9H8O2]

Yield

Conditions & References

30 %, 62 %

With oxone, 2-iodo-3,4,5,6-tetramethylbenzoic acid in water, acetonitrile, Time= 3h, T= 20 °C Moorthy, Jarugu Narasimha; Senapati, Kalyan; Parida, Keshaba Nanda; Jhulki, Samik; Sooraj, Kunnikuruvan; Nair, Nisanth N.; Journal of Organic Chemistry; vol. 76; nb. 23; (2011); p. 9593 - 9601 View in Reaxys

O

O

O

Br

O

O

Rx-ID: 28565219 View in Reaxys 44/182 Yield

Conditions & References With iodine, 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in water, Time= 4h, T= 20 °C Moorthy, Jarugu Narasimha; Senapati, Kalyan; Singhal, Nidhi; Tetrahedron Letters; vol. 50; nb. 21; (2009); p. 2493 - 2496 View in Reaxys

O Cl

Sn

O O

O

Rx-ID: 28642468 View in Reaxys 45/182 Yield

Conditions & References

97 %Chromat.

in toluene, Time= 3h, T= 110 °C , Inert atmosphere Kashiwabara, Taigo; Tanaka, Masato; Journal of Organic Chemistry; vol. 74; nb. 10; (2009); p. 3958 - 3961 View in Reaxys

S

S

O

S

S

S

O

S

O

O

S S

O

O

O

Rx-ID: 11280775 View in Reaxys 46/182 Yield 7 %, 15 %, 13 %, 24 %

Conditions & References With oxygen, 5,15,10,20-tetraphenylporphyrin in dichloromethane, 2,2,2-trifluoroethanol, T= -20 °C , Irradiation, Further byproducts.

Cermola, Flavio; Guaragna, Annalisa; Iesce, Maria Rosaria; Palumbo, Giovanni; Purcaro, Raffaella; Rubino, Maria; Tuzi, Angela; Journal of Organic Chemistry; vol. 72; nb. 26; (2007); p. 10075 - 10080 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

S

S

O

O

S S

S

O O

S

Rx-ID: 11280777 View in Reaxys 47/182 Yield

Conditions & References

35 %, 55 %

With oxygen, 5,15,10,20-tetraphenylporphyrin in dichloromethane, T= -20 °C , Irradiation Cermola, Flavio; Guaragna, Annalisa; Iesce, Maria Rosaria; Palumbo, Giovanni; Purcaro, Raffaella; Rubino, Maria; Tuzi, Angela; Journal of Organic Chemistry; vol. 72; nb. 26; (2007); p. 10075 - 10080 View in Reaxys O O

O

Rx-ID: 10110443 View in Reaxys 48/182 Yield

Conditions & References

70 %, 3 %

With dihydrogen peroxide, 1,5-dicyclohexyl imidazole, Mn(III)-salophen in dichloromethane, N,N-dimethyl-formamide, Time= 1.25h, T= 0 °C Liu, Shih-Yuan; Nocera, Daniel G.; Tetrahedron Letters; vol. 47; nb. 12; (2006); p. 1923 - 1926 View in Reaxys O O

O

O

Rx-ID: 10117800 View in Reaxys 49/182 Yield

Conditions & References With dihydrogen peroxide, 1,5-dicyclohexyl imidazole, Mn(III)-salophen in dichloromethane, N,N-dimethyl-formamide, Time= 1.25h, T= 0 °C , Title compound not separated from byproducts Liu, Shih-Yuan; Nocera, Daniel G.; Tetrahedron Letters; vol. 47; nb. 12; (2006); p. 1923 - 1926 View in Reaxys O

O

O

O

Rx-ID: 10292018 View in Reaxys 50/182 Yield 16 %

Conditions & References With ammonium cerium(IV) nitrate in acetonitrile, Time= 4h, T= 20 °C Zhang, Yang; Jiao, Jingliang; Flowers II, Robert A.; Journal of Organic Chemistry; vol. 71; nb. 12; (2006); p. 4516 - 4520 View in Reaxys OH

O

HO

O

Rx-ID: 25928396 View in Reaxys 51/182

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1-Phenyl-1,2-propanedione [C9H8O2]

Yield

Conditions & References

84 %

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran, dimethyl sulfoxide, Time= 2.8h, T= 20 °C Yadav; Biswas, Swapan Kumar; Srinivas; Synthesis; nb. 24; (2006); p. 4237 - 4241 View in Reaxys O

O

O

O

Rx-ID: 9580098 View in Reaxys 52/182 Yield

Conditions & References

93 %

With [(tris(1-pyrazolyl)borate)Ru(P(phenyl)3)(CH3CN)2]PF6 in toluene, Time= 5h, T= 100 °C Chang, Chia-Lung; Kumar, Manyam Praveen; Liu, Rai-Shung; Journal of Organic Chemistry; vol. 69; nb. 8; (2004); p.

2793 - 2796 View in Reaxys OH

O

O

O

Rx-ID: 13687678 View in Reaxys 53/182 Yield

Conditions & References Reaction Steps: 2 1: tetra-n-propylammonium perruthenate; N-methyl morpholine oxide / CH2Cl2 / 1 h / 25 °C 2: 93 percent / (tris(1-pyrazolyl)borate)RuPPh3(CH3CN)2PF6 / toluene / 5 h / 100 °C With 4-methyltetrahydro-1,4-oxazin-3-one, tetrapropylammonium perruthennate, [(tris(1-pyrazolyl)borate)Ru(P(phenyl)3) (CH3CN)2]PF6 in dichloromethane, toluene Chang, Chia-Lung; Kumar, Manyam Praveen; Liu, Rai-Shung; Journal of Organic Chemistry; vol. 69; nb. 8; (2004); p.

2793 - 2796 View in Reaxys O HO

O

Rx-ID: 13691437 View in Reaxys 54/182 Yield

Conditions & References Reaction Steps: 3 1: m-chloroperbenzoic acid / CH2Cl2 2: tetra-n-propylammonium perruthenate; N-methyl morpholine oxide / CH2Cl2 / 1 h / 25 °C 3: 93 percent / (tris(1-pyrazolyl)borate)RuPPh3(CH3CN)2PF6 / toluene / 5 h / 100 °C With 4-methyltetrahydro-1,4-oxazin-3-one, tetrapropylammonium perruthennate, [(tris(1-pyrazolyl)borate)Ru(P(phenyl)3) (CH3CN)2]PF6, 3-chloro-benzenecarboperoxoic acid in dichloromethane, toluene Chang, Chia-Lung; Kumar, Manyam Praveen; Liu, Rai-Shung; Journal of Organic Chemistry; vol. 69; nb. 8; (2004); p.

2793 - 2796 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O H

methylacetylene metal salt

O

O

Rx-ID: 13696535 View in Reaxys 55/182 Yield

Conditions & References Reaction Steps: 4 1: tetrahydrofuran / 2 h / 0 °C 2: m-chloroperbenzoic acid / CH2Cl2 3: tetra-n-propylammonium perruthenate; N-methyl morpholine oxide / CH2Cl2 / 1 h / 25 °C 4: 93 percent / (tris(1-pyrazolyl)borate)RuPPh3(CH3CN)2PF6 / toluene / 5 h / 100 °C With 4-methyltetrahydro-1,4-oxazin-3-one, tetrapropylammonium perruthennate, [(tris(1-pyrazolyl)borate)Ru(P(phenyl)3) (CH3CN)2]PF6, 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran, dichloromethane, toluene Chang, Chia-Lung; Kumar, Manyam Praveen; Liu, Rai-Shung; Journal of Organic Chemistry; vol. 69; nb. 8; (2004); p.

2793 - 2796 View in Reaxys O

O

Rx-ID: 6163021 View in Reaxys 56/182 Yield

Conditions & References Brown,R.F.C. et al.; Australian Journal of Chemistry; vol. 29; (1976); p. 1705 - 1712 View in Reaxys Dahn,H. et al.; Helvetica Chimica Acta; vol. 46; (1963); p. 1000 - 1006 View in Reaxys Wolfe,S. et al.; Canadian Journal of Chemistry; vol. 49; (1971); p. 1099 - 1105 View in Reaxys Bestmann,H.-J. et al.; Chemische Berichte; vol. 102; (1969); p. 2259 - 2269 View in Reaxys Wasserman,H.H.; Ives,J.L.; Journal of the American Chemical Society; vol. 98; (1976); p. 7868 - 7869 View in Reaxys De Kimpe,N. et al.; Tetrahedron; vol. 35; (1979); p. 789 - 798 View in Reaxys Otsuji,Y. et al.; Bulletin of the Chemical Society of Japan; vol. 44; (1971); p. 219 - 223 View in Reaxys Ogata,Y.; Takagi,K.; Bulletin of the Chemical Society of Japan; vol. 47; (1974); p. 2255 - 2259 View in Reaxys Bauer,D.P.; Macomber,R.S.; Journal of Organic Chemistry; vol. 40; (1975); p. 1990 - 1992 View in Reaxys Padwa,A. et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 3281 - 3287 View in Reaxys Ames,D.E. et al.; Journal of the Chemical Society [Section] C: Organic; (1968); p. 2617 - 2621 View in Reaxys Seebach,D.; Synthesis; (1969); p. 17 - 36 View in Reaxys Ferdinand,G.; Schank,K.; Synthesis; (1976); p. 404 - 405 View in Reaxys Oka,K.; Hara,S.; Tetrahedron Letters; (1977); p. 695 - 698 View in Reaxys Vereshchagin et al.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 15; (1979); p. 1247; Khimiya Geterotsiklicheskikh Soedinenii; vol. 11; (1979); p. 1552 View in Reaxys Mineo; Nakagawa; Yakugaku Zasshi; vol. 94; nb. 9; (1974); p. 1180 - 1182 View in Reaxys Leusen; Leusen; Tetrahedron Letters; (1977); p. 4233,4234 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

Birch et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1973); p. 1882,1891 View in Reaxys Corey; Erickson; Journal of Organic Chemistry; vol. 36; (1971); p. 3553,3558 View in Reaxys El-Hashash; El-Kady; Revue Roumaine de Chimie; vol. 23; (1978); p. 1581,1586 View in Reaxys Bailey et al.; Journal of the American Chemical Society; vol. 82; (1960); p. 6136,6140 View in Reaxys Colonge et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 259; (1964); p. 3566 View in Reaxys Nagao et al.; Tetrahedron Letters; (1978); p. 4115 View in Reaxys Langendries; Schryver; Tetrahedron Letters; (1972); p. 4781 View in Reaxys Brown et al.; Journal of the Chemical Society, Chemical Communications; (1975); p. 328 View in Reaxys Michalew et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 30; (1960); p. 3714,3679 View in Reaxys Heilmann; Baret; Comptes Rendus des Seances de l'Academie des Sciences, Serie D: Sciences Naturelles; vol. 267; nb. 8; (1968); p. 579 View in Reaxys Shevshuk et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 45; (1975); p. 2143,2109,2114 View in Reaxys Jones; Ritchie; Journal of the Chemical Society; (1960); p. 4141,4151 View in Reaxys Pepper; Saha; Canadian Journal of Chemistry; vol. 42; (1964); p. 113,116 View in Reaxys Yamashita; Suemitsu; Journal of the Chemical Society, Chemical Communications; (1977); p. 691 View in Reaxys Saito et al.; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 3198,3199,3201 View in Reaxys Shibata; Takase; Nippon Kagaku Kaishi; (1976); p. 1329 View in Reaxys Mc Lauchlan et al.; Molecular Physics; vol. 36; (1978); p. 1397,1400-1402 View in Reaxys Patent; Bratchanskii et al.; SU320163; (1977); Ref. Zh., Khim.; nb. 180119P; (1977) View in Reaxys Thibault; Annales de Chimie (Cachan, France); vol. 6; nb. 14; (1971); p. 381,382,386 View in Reaxys Bergeron; Hoffman; Journal of Organic Chemistry; vol. 44; (1979); p. 1835,1836 View in Reaxys Russell; Mikol; Journal of the American Chemical Society; vol. 88; (1966); p. 5498,5503 View in Reaxys Bailey et al.; Journal of Organic Chemistry; vol. 27; (1962); p. 1198 View in Reaxys Kotschetkow; Dudykina; J. Gen. Chem. USSR (Engl. Transl.); vol. 30; (1960); p. 3054,3027 View in Reaxys Dorokhova et al.; Pharmaceutical Chemistry Journal; vol. 9; nb. 5; (1975); p. 301,302,303; Khimiko-Farmatsevticheskii Zhurnal; vol. 9; nb. 5; (1975); p. 21 View in Reaxys Smith; Waters; Journal of the Chemical Society [Section] B: Physical Organic; (1969); p. 462 View in Reaxys Examples of such diketo compounds are: α-formylacetone, diacetyl, 4,5-dioxooctane, 1-phenyl-1,2-dioxopropane, 1-phenyl-2,3-dioxobutane, p-methoxydiphenylglyoxal,

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1-Phenyl-1,2-propanedione [C9H8O2]

1,2-cyclopentanedione, 1,2-cyclohexanedione, acetylacetone, ...

Patent; Rhodia Chimie; Centre National de la Recherche Scientifique (CNRS); US6610875; (2003); (B1) English View in Reaxys The following may be mentioned in particular as examples of diketonic compounds of formula (Va2): α-formylacetone, diacetyl, 3,4-dioxohexane, 4,5-dioxooctane, 1-phenyl-1,2-dioxopropane, 1-phenyl-2,3-dioxobutane, 1,2-cyclopentanedione, 1,2-cyclohexanedione, acetylacetone, ...

Patent; Rhodia Chimie; US6166257; (2000); (A) English View in Reaxys Process according to claim 12, wherein the ketonic compound of formula (Va2) is selected from: α-formylacetone, diacetyl, 3,4-dioxohexane, 4,5-dioxooctane, 1-phenyl-1,2-dioxopropane, 1-phenyl-2,3-dioxobutane, 1. 2-cyclopentanedione, 1,2-cyclohexanedione, acetylacetone, ...

Patent; Rhodia Chimie; US6166257; (2000); (A) English View in Reaxys XIII : A solution of 0.4 gram of biacetyl (0.014M) and 1.4 grams of 1-phenyl-1,2-propanedione (0.028M) in 250 milliliters of o-dichlorobenzene was charged to the pressure reactor.

EXAMPLE XIII A solution of 0.4 gram of biacetyl (0.014M) and 1.4 grams of 1-phenyl-1,2-propanedione (0.028M) in 250 milliliters of o-dichlorobenzene was charged to the pressure reactor.

Condensed propylene (45.6 grams, 3.20M) was added increasing the pressure to 80 psia.

Nitrogen was added to bring the pressure to 150 psia, and oxygen was added to a pressure of 169 psia.

Irradiation (450 Watt high pressure mercury lamp) of the vigorously stirred solution for 90 minutes produced 11.2 mmoles of propylene oxide (7.5 mmoles/hr.) as the only product.

Patent; Celanese Corporation; US4383904; (1983); (A) English View in Reaxys HO

O

O

N

O

Rx-ID: 668915 View in Reaxys 57/182 Yield 83 %

Conditions & References With chromium(VI) oxide, silica gel in toluene, Time= 4h, T= 72 - 75 °C , Oxidation, Deoximation Bendale, Pravin M.; Khadilkar, Bhushan M.; Synthetic Communications; vol. 30; nb. 4; (2000); p. 665 - 669 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

76 %

With manganese(IV) oxide, silica gel, Time= 0.1h, microwave irradiation Khadilkar, Bhushan M.; Madyar, Virendra R.; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 41; nb. 5; (2002); p. 1081 - 1082 View in Reaxys With sulfuric acid, beim Destillieren Kolb; Justus Liebigs Annalen der Chemie; vol. 291; (1896); p. 267 View in Reaxys Diels; vom Dorp; Chemische Berichte; vol. 36; (1903); p. 3190 View in Reaxys Borsche; Chemische Berichte; vol. 40; (1907); p. 743 View in Reaxys

O

S

O

S

O

Rx-ID: 1747690 View in Reaxys 58/182 Yield

Conditions & References With methyltriphenylphosphonium tribromide, water, 1.) THF, 48 h, room temperature; further reagents, solvents and times, Yield given. Multistep reaction Cristau, Henri-Jean; Bazbouz, Akram; Morand, Philippe; Torreilles, Eliane; Tetrahedron Letters; vol. 27; nb. 26; (1986); p.

2965 - 2966 View in Reaxys

43 % Chromat.

With bismuth(III) chloride, bismuth(III) nitrate, water in benzene, Time= 7h, T= 20 °C Komatsu, Naoki; Taniguchi, Azusa; Wada, Shinobu; Suzuki, Hitomi; Advanced Synthesis and Catalysis; vol. 343; nb. 5; (2001); p. 473 - 480 View in Reaxys O

HO

O

Rx-ID: 8811126 View in Reaxys 59/182 Yield 76 % Chromat.

Conditions & References With oxoammonium resin in dichloromethane, Time= 2h, T= 20 °C Weik, Steffen; Nicholson, Graeme; Jung, Gnther; Rademann, Jrg; Angewandte Chemie - International Edition; vol. 40; nb.

8; (2001); p. 1436 - 1439 View in Reaxys O

O

O

Rx-ID: 8863596 View in Reaxys 60/182 Yield 1 %, 77 %

Conditions & References With dimethyl sulfoxide, palladium dichloride, Time= 12h, T= 90 °C Yusubov; Filimonov; Chi, Ki-Whan; Russian Chemical Bulletin; vol. 50; nb. 4; (2001); p. 649 - 653 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O O

O

Rx-ID: 8734533 View in Reaxys 61/182 Yield

Conditions & References

95 %

With HOF* CH3CN in chloroform, T= 0 - 20 °C Dayan; Ben-David; Rozen; Journal of Organic Chemistry; vol. 65; nb. 25; (2000); p. 8816 - 8818 View in Reaxys polystyrene O

O O

Rx-ID: 5291416 View in Reaxys 62/182 Yield

Conditions & References With air, T= 400 - 650 °C , Formation of xenobiotics, Oxidation Park, Byung-Ik; Bozzelli, Joseph W.; Booty, Michael R.; Bernhard, Mary J.; Mesuere, Karel; Pettigrew, Charles A.; Shi, Ji-Chun; Simonich, Staci L.; Environmental Science and Technology; vol. 33; nb. 15; (1999); p. 2584 - 2592 View in Reaxys O

O O

O

O O

O

O

O

Rx-ID: 4664909 View in Reaxys 63/182 Yield

Conditions & References

10 %

With ozone in dichloromethane, T= -60 °C , Yields of byproduct given Griesbaum, Karl; Dong, Yuxiang; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 6; (1997); p. 575 - 577 View in Reaxys

O O O

O N

N

Rx-ID: 3676179 View in Reaxys 64/182 Yield 90 %

Conditions & References in pentane, Time= 1h, Irradiation Moss, Robert A.; Xue, Song; Liu, Weiguo; Journal of the American Chemical Society; vol. 116; nb. 4; (1994); p. 1583 - 1584 View in Reaxys in pentane, Time= 2h, T= 25 °C , Irradiation Moss, Robert A.; Xue, Song; Liu, Weiguo; Krogh-Jespersen, Karsten; Journal of the American Chemical Society; vol. 118; nb. 50; (1996); p. 12588 - 12597 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

O

HO

O

O

O

HO

O

Rx-ID: 4356811 View in Reaxys 65/182 Yield

Conditions & References With 3,3-dimethyldioxirane in dichloromethane, acetone, Time= 32h, T= 0 °C , Yield given. Yields of byproduct given Curci, Ruggero; D'Accolti, Lucia; Dinoi, Anna; Fusco, Caterina; Rosa, Angela; Tetrahedron Letters; vol. 37; nb. 1; (1996); p. 115 - 118 View in Reaxys

HO

O

HO

O

O

HO HO

H

O

Rx-ID: 4517751 View in Reaxys 66/182 Yield

Conditions & References

25 mg

With 3,3-dimethyldioxirane in acetone, Ambient temperature, Yield given. Title compound not separated from byproducts Bovicelli, Paolo; Sanetti, Anna; Lupattelli, Paolo; Tetrahedron; vol. 52; nb. 33; (1996); p. 10969 - 10978 View in Reaxys

25 mg

With 3,3-dimethyldioxirane in acetone, Ambient temperature, Yields of byproduct given Bovicelli, Paolo; Sanetti, Anna; Lupattelli, Paolo; Tetrahedron; vol. 52; nb. 33; (1996); p. 10969 - 10978 View in Reaxys

25 mg

With 3,3-dimethyldioxirane in dichloromethane, Time= 12h, Ambient temperature, other sec,sec 1,2-diols, Product distribution Bovicelli, Paolo; Sanetti, Anna; Lupattelli, Paolo; Tetrahedron; vol. 52; nb. 33; (1996); p. 10969 - 10978 View in Reaxys

HO

O

O

HO

Rx-ID: 306777 View in Reaxys 67/182 Yield

Conditions & References With nitric acid Zincke; Zahn; Chemische Berichte; vol. 43; (1910); p. 855 View in Reaxys

73 % Chromat.

With dihydrogen peroxide, PCWP in 1,2-dichloro-ethane, Time= 6h, Heating Iwahama, Takahiro; Sakaguchi, Satoshi; Nishiyama, Yutaka; Ishii, Yasutaka; Tetrahedron Letters; vol. 36; nb. 9; (1995); p.

1523 - 1526 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

O

P

O

Rx-ID: 3778591 View in Reaxys 68/182 Yield

Conditions & References

70 %

With triphenyl phosphite, ozone in dichloromethane, Time= 1.83333h, T= -78 °C Bestmann, Hans Juergen; Kumar, Kamlesh; Kisielowski, Lothar; Chemische Berichte; vol. 116; nb. 6; (1983); p. 2378 2382 View in Reaxys

42 %

With potassium permanganate, magnesium sulfate in toluene, Time= 40h, T= 50 - 60 °C Aitken, R. Alan; Cadogan, J. I. G.; Gosney, Ian; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 101; nb. 1-4; (1995); p. 281 - 286 View in Reaxys O

O O

O

HO HO

Rx-ID: 4161020 View in Reaxys 69/182 Yield

Conditions & References

79 %, 3 %

With oxygen, <Bi(III)(mandelate)2>2(μ-O) in dimethyl sulfoxide, Time= 72h, T= 95 °C Le Boisselier, Veronique; Coin, Christine; Postel, Michele; Dunach, Elisabet; Tetrahedron; vol. 51; nb. 17; (1995); p. 4991 4996 View in Reaxys

39 %, 30 %

With oxygen, <Bi(III)(mandelate)2>2(μ-O) in dimethyl sulfoxide, Time= 25h, T= 80 °C Le Boisselier, Veronique; Coin, Christine; Postel, Michele; Dunach, Elisabet; Tetrahedron; vol. 51; nb. 17; (1995); p. 4991 4996 View in Reaxys O

N N N

OH

O

O

O

HO

O

HO

N

N N

O

N N

O

N

N N N

Rx-ID: 4161610 View in Reaxys 70/182 Yield

Conditions & References

11 %, 3.8 % With acetaldehyde, 1,8-diazabicyclo[5.4.0]undec-7-ene, Time= 2.5h, T= 0 °C , Yields of byproduct given Patonay; Hoffman; Journal of Organic Chemistry; vol. 60; nb. 8; (1995); p. 2368 - 2377

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1-Phenyl-1,2-propanedione [C9H8O2]

View in Reaxys O N

O

N N

OH

O

O

O

HO

O

HO

N

N N

O

N N

O

N

N N N

Rx-ID: 4173746 View in Reaxys 71/182 Yield

Conditions & References

11 %, 3.8 % With 1,8-diazabicyclo[5.4.0]undec-7-ene, Time= 2.5h, T= 0 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Patonay; Hoffman; Journal of Organic Chemistry; vol. 60; nb. 8; (1995); p. 2368 - 2377 View in Reaxys 11 %, 3.8 % With 1,8-diazabicyclo[5.4.0]undec-7-ene, Time= 2.5h, T= 0 °C , Yields of byproduct given Patonay; Hoffman; Journal of Organic Chemistry; vol. 60; nb. 8; (1995); p. 2368 - 2377 View in Reaxys

O HO

O O N

Rx-ID: 4199992 View in Reaxys 72/182 Yield

Conditions & References

71 %

With 2,6-dimethylpyridine, methanesulfonyl chloride in dichloromethane, Time= 0.25h, T= 0 °C Patonay; Hoffman; Journal of Organic Chemistry; vol. 60; nb. 8; (1995); p. 2368 - 2377 View in Reaxys

O

P

O

O

Rx-ID: 4293612 View in Reaxys 73/182 Yield 43 %

Conditions & References With potassium permanganate, magnesium sulfate in toluene, Time= 40h, T= 50 - 60 °C Aitken, R. Alan; Cadogan, J. I. G.; Gosney, Ian; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 101; nb. 1-4; (1995); p. 281 - 286 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O Cl –

P+

hydroxylamine sulfate

O

Rx-ID: 18015720 View in Reaxys 74/182 Yield

Conditions & References Reaction Steps: 2 1: 1.) n-BuLi / 1.) toluene, hexane, 15 min, 2.) toluene, hexane, 3 h 2: 43 percent / KMnO4, aq. MgSO4 / toluene / 40 h / 50 - 60 °C With potassium permanganate, n-butyllithium, magnesium sulfate in toluene Aitken, R. Alan; Cadogan, J. I. G.; Gosney, Ian; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 101; nb. 1-4; (1995); p. 281 - 286 View in Reaxys O

O

water

hydroxylamine sulfate

O

Cl

Rx-ID: 18019207 View in Reaxys 75/182 Yield

Conditions & References Reaction Steps: 2 1: 1.) n-BuLi / 1.) toluene, hexane, 15 min, 2.) toluene, hexane, 3 h 2: 42 percent / KMnO4, aq. MgSO4 / toluene / 40 h / 50 - 60 °C With potassium permanganate, n-butyllithium, magnesium sulfate in toluene Aitken, R. Alan; Cadogan, J. I. G.; Gosney, Ian; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 101; nb. 1-4; (1995); p. 281 - 286 View in Reaxys O

C O

O O

Rx-ID: 3675650 View in Reaxys 76/182 Yield

Conditions & References in pentane, Time= 1h, Irradiation, Rate constant Moss, Robert A.; Xue, Song; Liu, Weiguo; Journal of the American Chemical Society; vol. 116; nb. 4; (1994); p. 1583 - 1584 View in Reaxys

O

O N N

O

Rx-ID: 4001134 View in Reaxys 77/182 Yield

Conditions & References With ozone in dichloromethane, T= -78 °C Dell'Erba, Carlo; Novi, Marino; Petrillo, Giovanni; Tavani, Cinzia; Tetrahedron; vol. 50; nb. 38; (1994); p. 11239 - 11248 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

2-hydroxy-2-phenyl-butyraldehyde-oxime O

hydroxylamine sulfate

O

Rx-ID: 18280318 View in Reaxys 78/182 Yield

Conditions & References Reaction Steps: 3 1: 48 percent / KOtBu / dimethylsulfoxide / Ambient temperature 2: dimethylsulfoxide / Ambient temperature 3: O3 / CH2Cl2 / -78 °C With potassium tert-butylate, ozone in dichloromethane, dimethyl sulfoxide Dell'Erba, Carlo; Novi, Marino; Petrillo, Giovanni; Tavani, Cinzia; Tetrahedron; vol. 50; nb. 38; (1994); p. 11239 - 11248 View in Reaxys

O

O N N H

hydroxylamine sulfate

O

Rx-ID: 18289398 View in Reaxys 79/182 Yield

Conditions & References Reaction Steps: 2 1: dimethylsulfoxide / Ambient temperature 2: O3 / CH2Cl2 / -78 °C With ozone in dichloromethane, dimethyl sulfoxide Dell'Erba, Carlo; Novi, Marino; Petrillo, Giovanni; Tavani, Cinzia; Tetrahedron; vol. 50; nb. 38; (1994); p. 11239 - 11248 View in Reaxys O

Cl

O O

O

Rx-ID: 2013134 View in Reaxys 80/182 Yield

Conditions & References

10 %

With tris(2,4-dibromophenyl)aminium hexachloroantimonate in dichloromethane, Time= 0.25h, Ambient temperature Lopez, Luigi; Mele, Giuseppe; Nacci, Angelo; Troisi, Luigino; Tetrahedron Letters; vol. 34; nb. 24; (1993); p. 3897 - 3900 View in Reaxys

OH

H

O

O

HO H

O

HO HO

H

O

Rx-ID: 2103547 View in Reaxys 81/182 Yield

Conditions & References With 3,3-dimethyldioxirane in dichloromethane, acetone, Time= 22h, T= 0 °C , Yield given. Yields of byproduct given

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1-Phenyl-1,2-propanedione [C9H8O2]

D'Accolti, Lucia; Detomaso, Antonia; Fusco, Caterina; Rosa, Angela; Curci, Ruggero; Journal of Organic Chemistry; vol.

58; nb. 14; (1993); p. 3600 - 3601 View in Reaxys O

O O

Cl

H

N

N H

O HO

Rx-ID: 2428150 View in Reaxys 82/182 Yield

Conditions & References With carboxymethylcellulose, T= 48 °C , Product distribution Retuert; Yazdani-Pedram; Farmaco; vol. 47; nb. 5; (1992); p. 649 - 660 View in Reaxys O

HO H

O O O

Rx-ID: 1977850 View in Reaxys 83/182 Yield

Conditions & References With oxygen, 5,15,10,20-tetraphenylporphyrin in tetrachloromethane, Ambient temperature, Irradiation, other arylallenes, Mechanism Erden; Martinez; Tetrahedron Letters; vol. 32; nb. 16; (1991); p. 1859 - 1862 View in Reaxys O

S

O

O

Rx-ID: 2188731 View in Reaxys 84/182 Yield

Conditions & References

91 %

With CuCl2*2H2O in water, acetone, Heating Ishibashi; Matsuoka; Ikeda; Chemical and Pharmaceutical Bulletin; vol. 39; nb. 7; (1991); p. 1854 - 1856 View in Reaxys

O O

O N

O

O

Rx-ID: 3577864 View in Reaxys 85/182 Yield 49 %

Conditions & References With triethylamine, tetrakis(triphenylphosphine) palladium(0) in benzene, Time= 10h, Heating Vankar, Yashwant D.; Singh, Surendra P.; Chemistry Letters; (1986); p. 1939 - 1942 View in Reaxys

49 %

With tetrakis(triphenylphosphine) palladium(0), triethylamine in benzene, Time= 10h, Heating Vankar, Yashwant D.; Shah, Kavita; Bawa, Anita; Singh, Surendra P.; Tetrahedron; vol. 47; nb. 42; (1991); p. 8883 - 8906 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

O S

O S

Rx-ID: 1737431 View in Reaxys 86/182 Yield

Conditions & References

82 %

in water, acetonitrile, electrolysis; Pt-electrode Martre, Anne-Marie; Mousset, Guy; Rhlid, Rachid Bel; Veschambre, Henri; Tetrahedron Letters; vol. 31; nb. 18; (1990); p.

2599 - 2602 View in Reaxys O

O O

O

Rx-ID: 2157560 View in Reaxys 87/182 Yield

Conditions & References With hydrogenchloride in tetrahydrofuran, Time= 16h, Ambient temperature Kwon, Hyok Boong; McKee, Blain H.; Stille, J. K.; Journal of Organic Chemistry; vol. 55; nb. 10; (1990); p. 3114 - 3118 View in Reaxys

O O

Br– O

P+

Cl

Rx-ID: 2707590 View in Reaxys 88/182 Yield

Conditions & References Yield given. Multistep reaction Davis, Franklin A.; Chen, Bang-chi; Journal of Organic Chemistry; vol. 55; nb. 1; (1990); p. 360 - 363 View in Reaxys O

F

F

O

Rx-ID: 2149575 View in Reaxys 89/182 Yield 53 %

Conditions & References With potassium permanganate in water, acetone, Time= 2h, T= 20 °C Zeifman, Yu. V.; Postovoi, S. A.; Delyagina, N. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 3.2; (1989); p. 664 - 666; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb.

3; (1989); p. 738 - 740 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

O

O

O

O

S N

O

S

Br

NH

O

O

O

Rx-ID: 3399008 View in Reaxys 90/182 Yield

Conditions & References With mercury(II) diacetate in water, acetic acid, T= 44.9 °C , variation of temperature, effect of concentration; ΔH(excit), ΔS(excit), αG(excit), Kinetics, Mechanism, Thermodynamic data Mohan, K. Vijaya; Rao, P. Raghunath; Sundaram, E. V.; Journal of the Indian Chemical Society; vol. 65; (1988); p. 91 - 93 View in Reaxys

F

O O

HO O

F F

O

F

F F

F

O

O

F F

O

O

O

Rx-ID: 1548610 View in Reaxys 91/182 Yield

Conditions & References With nitrobenzene, Time= 1h, Ambient temperature, var. acetylene/nitrobenzene ratio, Product distribution Stavber, Stojan; Zupan, Marko; Journal of Organic Chemistry; vol. 52; nb. 22; (1987); p. 5022 - 5025 View in Reaxys O

O

O

O

O

O

O

O

O

Rx-ID: 1548748 View in Reaxys 92/182 Yield

Conditions & References With oxygen, T= 110 °C , p= 759.8Torr , autoxidation reactions of different acetylenic hydrocarbons to other α-dicarbonyl compounds, Mechanism, Product distribution Rao, T. S. S.; Pritzkow, W.; Journal fuer Praktische Chemie (Leipzig); vol. 329; nb. 3; (1987); p. 474 - 482 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O F

O

O

F F

O

O

F

F

O

F

Rx-ID: 1548765 View in Reaxys 93/182 Yield

Conditions & References

10 %, 10 %, With methanol, caesium fluoroxysulphate, Time= 1h, Ambient temperature, Further byproducts given 15 %, 5 % Stavber, Stojan; Zupan, Marko; Journal of Organic Chemistry; vol. 52; nb. 22; (1987); p. 5022 - 5025 View in Reaxys O

O

O

O

O

H

O

O O

O O

Rx-ID: 3971682 View in Reaxys 94/182 Yield

Conditions & References

6 %, 8 %, 81 %

With cobalt(II) chloride in acetonitrile, Time= 24h, Ambient temperature, Product distribution, Mechanism Ahmad, Saeed; Iqbal, Javed; Journal of the Chemical Society, Chemical Communications; (1987); p. 692 - 693 View in Reaxys

6 %, 8 %, 81 %

With cobalt(II) chloride in acetonitrile, Time= 24h, Ambient temperature Ahmad, Saeed; Iqbal, Javed; Journal of the Chemical Society, Chemical Communications; (1987); p. 692 - 693 View in Reaxys

45 %, 65 %, With cobalt(II) chloride in acetonitrile, Time= 24h, Ambient temperature 12 % Ahmad, Saeed; Iqbal, Javed; Journal of the Chemical Society, Chemical Communications; (1987); p. 692 - 693 View in Reaxys

O O

O O

Sn

Cl

Rx-ID: 3978447 View in Reaxys 95/182 Yield 75 %

Conditions & References With hydrogenchloride, bis-triphenylphosphine-palladium(II) chloride in benzene, Time= 20h, T= 100 °C Kosugi, Masanori; Sumiya, Takashi; Obara, Yukimasa; Suzuki, Motohiro; Sano, Hiroshi; Migita, Toshihiko; Bulletin of the Chemical Society of Japan; vol. 60; nb. 2; (1987); p. 767 - 768 View in Reaxys O O

O

HO O

O

OH

O

Rx-ID: 1575948 View in Reaxys 96/182 Yield 87 % Spectr.

Conditions & References With dimethyl sulfide-d6, ozone, 1) CDCl3Cl2CHCHCl2 -50 deg C, 2) r.t., 30 min, Product distribution Griesbaum, Karl; Zwick, Gerhard; Chemische Berichte; vol. 119; nb. 1; (1986); p. 229 - 243 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

HO O

HO

O

O

O

O

O

OH O

OH

O O

Rx-ID: 1575949 View in Reaxys 97/182 Yield

Conditions & References

29 % Spectr., 71 % Spectr., 25 % Spectr., 70 % Spectr.

With ozone in chloroform-d1, T= -50 °C , Product distribution Griesbaum, Karl; Zwick, Gerhard; Chemische Berichte; vol. 119; nb. 1; (1986); p. 229 - 243 View in Reaxys

O

HO O

O

O O

O

O O

O OH

O O

OH

O

O HO

Rx-ID: 1579222 View in Reaxys 98/182 Yield 10 % Spectr., 12 % Spectr., 26 % Spectr., 30 % Spectr., 14 % Spectr., 67 % Spectr.

Conditions & References With ozone in chloroform-d1, Time= 27h, Ambient temperature, Product distribution Griesbaum, Karl; Zwick, Gerhard; Chemische Berichte; vol. 119; nb. 1; (1986); p. 229 - 243 View in Reaxys

O

O O

O

HO O

OH

O

Rx-ID: 1579223 View in Reaxys 99/182 Yield 85 % Spectr.

Conditions & References With dimethyl sulfide-d6, ozone, 1) CDCl3, Cl2CHCHCl2, -50 deg C, 2) r.t., 20 min, Product distribution Griesbaum, Karl; Zwick, Gerhard; Chemische Berichte; vol. 119; nb. 1; (1986); p. 229 - 243 View in Reaxys

O

O

O

HO O

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1-Phenyl-1,2-propanedione [C9H8O2]

O O

O

O

O

OH

O

O

OH

O

O

O

Rx-ID: 1581912 View in Reaxys 100/182 Yield

Conditions & References

20 % With ozone in chloroform-d1, Time= 2h, Ambient temperature, further time: 24 h, Product distribution, Mechanism Spectr., 28 Griesbaum, Karl; Zwick, Gerhard; Chemische Berichte; vol. 119; nb. 1; (1986); p. 229 - 243 % Spectr., View in Reaxys 40 % Spectr., 18 % Spectr., 10 % Spectr., 3 % Spectr.

O O

O

HO O

OH

O

Rx-ID: 1581913 View in Reaxys 101/182 Yield

Conditions & References

90 % Spectr.

With 2,3-dimercapto-succinic acid, ozone, 1) CDCl3, Cl2CHCHCl2, -50 deg C, 2) -40 deg C -> 0 deg C, 15 h, Product distribution Griesbaum, Karl; Zwick, Gerhard; Chemische Berichte; vol. 119; nb. 1; (1986); p. 229 - 243 View in Reaxys

O

HO

HO O

O O

O O

O

O

O

OH

O

O

Rx-ID: 1598914 View in Reaxys 102/182 Yield

Conditions & References

7 % Spectr., With dimethyl sulfide-d6, ozone, 1) CDCl3, Cl2CHCHCl2, -50 deg C, 2) r.t., 30 min, Product distribution 5 % Spectr., Griesbaum, Karl; Zwick, Gerhard; Chemische Berichte; vol. 119; nb. 1; (1986); p. 229 - 243 84 % View in Reaxys Spectr.

HO O O

HO

O O

O

O

O

OH

O

O

Rx-ID: 1598916 View in Reaxys 103/182

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1-Phenyl-1,2-propanedione [C9H8O2]

Yield

Conditions & References

6 % Spectr., With dimethyl sulfide-d6, ozone, 1) CDCl3, Cl2CHCHCl2, -50 deg C, 2) r.t., 1 h, Product distribution 88 % Griesbaum, Karl; Zwick, Gerhard; Chemische Berichte; vol. 119; nb. 1; (1986); p. 229 - 243 Spectr.

View in Reaxys O

O

O

O OH

O

OH

O

Rx-ID: 1982239 View in Reaxys 104/182 Yield

Conditions & References

19 % Spectr., 81 % Spectr., 80 % Spectr.

With ozone in methanol, chloroform-d1, T= -50 °C , Product distribution Griesbaum, Karl; Zwick, Gerhard; Chemische Berichte; vol. 119; nb. 1; (1986); p. 229 - 243 View in Reaxys

O O

O

O

OH

O

Rx-ID: 2124191 View in Reaxys 105/182 Yield

Conditions & References With dimethylsulfide, ozone, 1) CDCl3, -50 deg C, 2) -40 deg C -> 0 deg C, 15 h, Yield given. Multistep reaction. Yields of byproduct given Griesbaum, Karl; Zwick, Gerhard; Chemische Berichte; vol. 119; nb. 1; (1986); p. 229 - 243 View in Reaxys O O

HO

O

O

O

O

O

Rx-ID: 2158014 View in Reaxys 106/182 Yield

Conditions & References

4 % Spectr., With dimethyl sulfide-d6 in chloroform-d1, Product distribution 96 % Griesbaum, Karl; Zwick, Gerhard; Chemische Berichte; vol. 119; nb. 1; (1986); p. 229 - 243 Spectr.

View in Reaxys O

O HO

HO

O

Rx-ID: 3114749 View in Reaxys 107/182 Yield

Conditions & References in water, T= 25 °C , Equilibrium constant Segretario, James P.; Sleszynski, Neal; Partch, Richard E.; Zuman, Petr; Horak, Vaclav; Journal of Organic Chemistry; vol. 51; nb. 26; (1986); p. 5393 - 5396 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

O

N

O

Rx-ID: 2086354 View in Reaxys 108/182 Yield

Conditions & References

68 %

With bisacenaphthalenethiophene, oxygen in dichloromethane, Time= 0.666667h, T= -78 °C , Irradiation Wasserman, Harry H.; Ives, Jeffrey L.; Journal of Organic Chemistry; vol. 50; nb. 19; (1985); p. 3573 - 3580 View in Reaxys O

O O

O

O

Rx-ID: 2089065 View in Reaxys 109/182 Yield

Conditions & References

87 %

With sulfuric acid, Heating Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys O

O O

O

O

Rx-ID: 2551396 View in Reaxys 110/182 Yield

Conditions & References With sulfuric acid, Heating Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys

O

O O

O O

Rx-ID: 2834795 View in Reaxys 111/182 Yield

Conditions & References With sulfuric acid, Heating Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

O O

O

O

Rx-ID: 2839744 View in Reaxys 112/182 Yield

Conditions & References With sulfuric acid, Heating Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys O

O O

O

O

Rx-ID: 2846202 View in Reaxys 113/182 Yield

Conditions & References With sulfuric acid, Heating Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys O

O

HO

O

HO

O

O

Rx-ID: 2847437 View in Reaxys 114/182 Yield

Conditions & References With sulfuric acid, Heating Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys O

O N

O

N

O

O

Rx-ID: 2963828 View in Reaxys 115/182 Yield

Conditions & References With hydrogenchloride, Yield given Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O O

O S

O

Rx-ID: 3123153 View in Reaxys 116/182 Yield

Conditions & References

83 %

With silver(I) nitrite, iodine in diethyl ether, water, Time= 5.5h, Ambient temperature Fuji, Kaoru; Ueda, Masaru; Sumi, Kenzo; Fujita, Eiichi; Journal of Organic Chemistry; vol. 50; nb. 5; (1985); p. 662 - 666 View in Reaxys

83 %

With cyanogen iodide Fuji, Kaoru; Ueda, Masaru; Fujita, Eiichi; Journal of the Chemical Society, Chemical Communications; nb. 1; (1983); p. 49 50 View in Reaxys O O O

N N

N

OH F O

O

HN

O N

O

N

O

O OH F O

O

Rx-ID: 3174242 View in Reaxys 117/182 Yield

Conditions & References in potassium hydroxide, Time= 0.166667h, Ambient temperature, hydrolyses (in AGJ :half-life >20 h; in AIJ :half-life >20 h); taken for complete hydrolysis in 40 percent mouse blood : 150 min; Sakamoto; Ikeda; Kondo; Tsukamoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 11; (1985); p. 4870 - 4877 View in Reaxys Cl

O

O

O H 2N

S

NH O

S

O O

O

Rx-ID: 3616071 View in Reaxys 118/182 Yield

Conditions & References With acetic acid, Time= 16h, Heating Pusino, Alba; Saba, Antonio; Desole, Giuseppe; Rosnati, Vittorio; Gazzetta Chimica Italiana; vol. 115; nb. 1; (1985); p. 33 36

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1-Phenyl-1,2-propanedione [C9H8O2]

View in Reaxys

O

Ph3Sb 74 percent

O HO

H

O

Rx-ID: 6218233 View in Reaxys 119/182 Yield

Conditions & References

44 %

With triphenylantimony dibromide, 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane, Time= 18h, Ambient temperature Akiba, Kin-ya; Ohnari, Hideyuki; Ohkata, Katsuo; Chemistry Letters; (1985); p. 1577 - 1580 View in Reaxys O

O Cl

Cl

O

Rx-ID: 11716326 View in Reaxys 120/182 Yield

Conditions & References Reaction Steps: 2 1: sulfur / benzene / 1 h / 25 - 60 °C 2: dilute hydrochloric acid With hydrogenchloride, sulfur in benzene Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys Reaction Steps: 2 1: 76 percent / propan-1-ol / 1.) 2 h, r.t., 2.) 1 h, 30-35 deg C 2: aq. sulfuric acid / Heating With sulfuric acid in propan-1-ol Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys Reaction Steps: 2 1: 61 percent / butan-1-ol / 1.) 2 h, r.t., 2.) 1 h, 30-35 deg C 2: aq. sulfuric acid / Heating With sulfuric acid in butan-1-ol Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys Reaction Steps: 2 1: 67 percent / ethanol / 1.) 2 h, r.t., 2.) 1 h, 30-35 deg C 2: aq. sulfuric acid / Heating With sulfuric acid in ethanol Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys Reaction Steps: 2 1: 58 percent / propan-2-ol / 1.) 2 h, r.t., 2.) 1 h, 30-35 deg C

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1-Phenyl-1,2-propanedione [C9H8O2]

2: aq. sulfuric acid / Heating With sulfuric acid in isopropyl alcohol Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys Reaction Steps: 2 1: 67 percent / ethane-1,2-diol / 1.) 2 h, r.t., 2.) 1 h, 30-35 deg C 2: aq. sulfuric acid / Heating With sulfuric acid in ethylene glycol Bratchanskii, P. E.; Komissarova, G. G.; Esipov, G. V.; Journal of Organic Chemistry USSR (English Translation); vol. 21; nb. 10; (1985); p. 1961 - 1964; Zhurnal Organicheskoi Khimii; vol. 21; nb. 10; (1985); p. 2143 - 2147 View in Reaxys O

Cl O

O

O

S N H

O

Rx-ID: 18869771 View in Reaxys 121/182 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: CH3COOH / 16 h / Heating With acetic acid in diethyl ether Pusino, Alba; Saba, Antonio; Desole, Giuseppe; Rosnati, Vittorio; Gazzetta Chimica Italiana; vol. 115; nb. 1; (1985); p. 33 36 View in Reaxys Reaction Steps: 3 1: diethyl ether 2: 0.23M HCl / CHCl3 3: CH3COOH / 16 h / Heating With hydrogenchloride, acetic acid in diethyl ether, chloroform Pusino, Alba; Saba, Antonio; Desole, Giuseppe; Rosnati, Vittorio; Gazzetta Chimica Italiana; vol. 115; nb. 1; (1985); p. 33 36 View in Reaxys N N

O O

NH O

O

S O

Rx-ID: 18890945 View in Reaxys 122/182 Yield

Conditions & References Reaction Steps: 2 1: 0.23M HCl / CHCl3 2: CH3COOH / 16 h / Heating With hydrogenchloride, acetic acid in chloroform

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1-Phenyl-1,2-propanedione [C9H8O2]

Pusino, Alba; Saba, Antonio; Desole, Giuseppe; Rosnati, Vittorio; Gazzetta Chimica Italiana; vol. 115; nb. 1; (1985); p. 33 36 View in Reaxys O O

platinum

O

Rx-ID: 19833558 View in Reaxys 123/182 Yield

Conditions & References Reaction Steps: 2 1: 81 percent / 18 h / 55 °C 2: 68 percent / O2, bisacenaphthalenethiophene (BANT) / CH2Cl2 / 0.67 h / -78 °C / Irradiation With bisacenaphthalenethiophene, oxygen in dichloromethane Wasserman, Harry H.; Ives, Jeffrey L.; Journal of Organic Chemistry; vol. 50; nb. 19; (1985); p. 3573 - 3580 View in Reaxys O

Br

O

O

Rx-ID: 2018669 View in Reaxys 124/182 Yield

Conditions & References With t-butyl bromide in dimethyl sulfoxide, Time= 5h, T= 65 °C Armani, E.; Dossena, A.; Marchelli, R.; Casnati, G.; Tetrahedron; vol. 40; nb. 11; (1984); p. 2035 - 2040 View in Reaxys

O

Cl

O

OH

O

O

O O

O

O

O

O

O

Cl

O

O

O

Rx-ID: 2882540 View in Reaxys 125/182 Yield

Conditions & References Time= 24h, T= 120 °C , Yield given. Yields of byproduct given Pusino, A.; Rosnati, V.; Saba, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1893 - 1900 View in Reaxys With lithium acetate, Time= 15h, T= 90 °C , other reagents, Rate constant, Product distribution Pusino, A.; Rosnati, V.; Saba, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1893 - 1900 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O O

OH

2

H O

Cl O

O O

O

O

O

Cl

O

Rx-ID: 2882577 View in Reaxys 126/182 Yield

Conditions & References With lithium acetate, Time= 15h, T= 100 °C , other reagents, Rate constant, Product distribution Pusino, A.; Rosnati, V.; Saba, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1893 - 1900 View in Reaxys O

Br

O

O

O

Rx-ID: 3756883 View in Reaxys 127/182 Yield

Conditions & References With t-butyl bromide in dimethyl sulfoxide, Time= 5h, T= 65 °C Armani, E.; Dossena, A.; Marchelli, R.; Casnati, G.; Tetrahedron; vol. 40; nb. 11; (1984); p. 2035 - 2040 View in Reaxys

O

O

O

N

O

N

Rx-ID: 20791917 View in Reaxys 128/182 Yield

Conditions & References Reaction Steps: 2 2: LiOAc / 15 h / 90 °C / other reagents With lithium acetate Pusino, A.; Rosnati, V.; Saba, A.; Tetrahedron; vol. 40; nb. 10; (1984); p. 1893 - 1900 View in Reaxys O

N HO

Cl O

HO

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1-Phenyl-1,2-propanedione [C9H8O2]

O

O

O

H N

Cl N H

O

OH

O

Rx-ID: 1829230 View in Reaxys 129/182 Yield

Conditions & References

54 %, 23 %, in dichloromethane, Time= 0.75h, T= -60 °C 21 % Hino, Tohru; Yamaguchi, Hitoshi; Matsuki, Kenji; Nakano, Kumiko; Sodeoka, Mikiko; Nakagawa, Masako; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 1; (1983); p. 141 - 146 View in Reaxys

N

HO

O

O

O

H N

Cl N H

O

OH

O

Rx-ID: 1829232 View in Reaxys 130/182 Yield

Conditions & References

54 %, 23 %, With 3-chloro-benzenecarboperoxoic acid in dichloromethane, Time= 0.75h, T= -60 °C 21 % Hino, Tohru; Yamaguchi, Hitoshi; Matsuki, Kenji; Nakano, Kumiko; Sodeoka, Mikiko; Nakagawa, Masako; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 1; (1983); p. 141 - 146 View in Reaxys O

O O

O

Rx-ID: 2115511 View in Reaxys 131/182 Yield

Conditions & References

75 %

With hydrogenchloride in acetone, Time= 2.5h, Heating Soderquist, John A.; Leong, William Wei-Hwa; Tetrahedron Letters; vol. 24; nb. 23; (1983); p. 2361 - 2362 View in Reaxys

O

P

P

O O

O

Rx-ID: 3778594 View in Reaxys 132/182 Yield

Conditions & References With ozone in dichloromethane, T= -100 - -80 °C Caminade, A. M.; Khatib, F. el; Koenig, M.; Phosphorus and Sulfur and the Related Elements; vol. 14; (1983); p. 381 - 384

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1-Phenyl-1,2-propanedione [C9H8O2]

View in Reaxys O O

lead sulfide

O

Cl

Rx-ID: 19974564 View in Reaxys 133/182 Yield

Conditions & References Reaction Steps: 2 1: 64 percent / toluene / 4 h / Heating 2: 70 percent / P(OC6H5)3, O3 / CH2Cl2 / 1.83 h / -78 °C With triphenyl phosphite, ozone in dichloromethane, toluene Bestmann, Hans Juergen; Kumar, Kamlesh; Kisielowski, Lothar; Chemische Berichte; vol. 116; nb. 6; (1983); p. 2378 2382 View in Reaxys O

O

O 5-benzoyl-O 1,O 2-isopropyliden-α-D-arabinofuranose

O

Cl

Rx-ID: 21547747 View in Reaxys 134/182 Yield

Conditions & References Reaction Steps: 2 1: 73 percent / benzyl(chloro) bis-triphenylphosphinepalladium(II) / benzene / 1 h / Heating 2: 75 percent / 1.0 M HCl / acetone / 2.5 h / Heating With hydrogenchloride, <t-PhCH2(Cl)Pd(PPh3)2> in acetone, benzene Soderquist, John A.; Leong, William Wei-Hwa; Tetrahedron Letters; vol. 24; nb. 23; (1983); p. 2361 - 2362 View in Reaxys O

HO O

O O

O

O

HO HO

O O

Rx-ID: 1548609 View in Reaxys 135/182 Yield 21 % Chromat., 0 % Chromat., 9.3 % Chromat., 21 % Chromat., 24 % Chromat.

Conditions & References With peroxomonophosphoric acid in acetonitrile, Time= 24h, Ambient temperature, Product distribution Ogata, Yoshiro; Sawaki, Yasuhiko; Ohno, Takashi; Journal of the American Chemical Society; vol. 104; nb. 1; (1982); p. 216 - 219 View in Reaxys

O O

O

HO HO

O

Rx-ID: 1548758 View in Reaxys 136/182

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1-Phenyl-1,2-propanedione [C9H8O2]

Yield

Conditions & References

1.7 % Chromat., 39 % Chromat., 20 % Chromat.

With peroxomonophosphoric acid in acetonitrile, Time= 4h, Ambient temperature, Product distribution Ogata, Yoshiro; Sawaki, Yasuhiko; Ohno, Takashi; Journal of the American Chemical Society; vol. 104; nb. 1; (1982); p. 216 - 219 View in Reaxys

O O

HO

O

H O O

Si

O

O

Si

O

Rx-ID: 2571261 View in Reaxys 137/182 Yield

Conditions & References in hexane, Heating Saito, Isao; Nagata, Ryu; Kotsuki, Hiyoshizo; Matsuura, Teruo; Tetrahedron Letters; vol. 23; nb. 16; (1982); p. 1717 - 1720 View in Reaxys

O O

S

S

OH

O

O

Cl O O

O

Rx-ID: 2880908 View in Reaxys 138/182 Yield

Conditions & References

55 % Chromat.

Time= 0.666667h, T= 120 °C , other reagent (AcOK) and time, Product distribution Pusino, Alba; Rosnati, Vittorio; Saba, Antonio; Franco, Andrea; Gazzetta Chimica Italiana; vol. 112; nb. 11/12; (1982); p.

475 - 482 View in Reaxys

Cl

Cl

Cl

O

F

O O

O

Rx-ID: 2067883 View in Reaxys 139/182 Yield

Conditions & References With silver tetrafluoroborate in diethyl ether, 1) -50 deg C, 2) r.t., 1 h, Yield given. Yields of byproduct given Griesbaum, Karl; Keul, Helmut; Kibar, Riza; Pfeffer, Bernd; Spraul, Manfred; Chemische Berichte; vol. 114; nb. 5; (1981); p. 1858 - 1870 View in Reaxys Cl

Cl

O

O

Rx-ID: 20631702 View in Reaxys 140/182 Yield

Conditions & References Reaction Steps: 2 1: 1) m-chloroperbenzoic acid / 1) CH2Cl2, reflux, 18 h, 2) 140 deg C, 1 h 2: AgBF4 / diethyl ether / 1) -50 deg C, 2) r.t., 1 h

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1-Phenyl-1,2-propanedione [C9H8O2]

With silver tetrafluoroborate, 3-chloro-benzenecarboperoxoic acid in diethyl ether Griesbaum, Karl; Keul, Helmut; Kibar, Riza; Pfeffer, Bernd; Spraul, Manfred; Chemische Berichte; vol. 114; nb. 5; (1981); p. 1858 - 1870 View in Reaxys Reaction Steps: 2 1: m-chloroperbenzoic acid / CH2Cl2 / 18 h / Heating 2: AgBF4 / diethyl ether / 1) -50 deg C, 2) r.t., 1 h With silver tetrafluoroborate, 3-chloro-benzenecarboperoxoic acid in diethyl ether, dichloromethane Griesbaum, Karl; Keul, Helmut; Kibar, Riza; Pfeffer, Bernd; Spraul, Manfred; Chemische Berichte; vol. 114; nb. 5; (1981); p. 1858 - 1870 View in Reaxys

O O

Cl

O–

O

Na +

O

Cl

O

O

Rx-ID: 2064822 View in Reaxys 141/182 Yield

Conditions & References

67 % Chromat., 7 % Chromat.

in isopropyl alcohol, Ambient temperature Kimpe, Norbert De; Verhe, Roland; Buyck, Laurent De; Schamp, Niceas; Journal of Organic Chemistry; vol. 45; nb. 14; (1980); p. 2803 - 2813 View in Reaxys O

O

Cl

H

N H

N

O

Rx-ID: 2428151 View in Reaxys 142/182 Yield

Conditions & References With hydrogenchloride, potassium chloride in water, Time= 96h, T= 45 °C , hydrolysis, pH dependence, Product distribution, Mechanism Walters; Journal of Pharmaceutical Sciences; vol. 69; nb. 10; (1980); p. 1206 - 1209 View in Reaxys O

O

O (v8)

N O N(v4) Os O (v4)

O

(v4)

O (v4)N O (v8)Os N

O

O

Rx-ID: 26756477 View in Reaxys 143/182 Yield

Conditions & References With sodium sulfite vol. Os: SVol.1; 4.1.3.1.2.4, page 203 - 204 ; (from Gmelin) View in Reaxys With Na2SO3 Schroeder, M.; Griffith, W. P.; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); (1978); p. 1599 - 1602 ; (from Gmelin) View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

O

O

N

Rx-ID: 1415739 View in Reaxys 144/182 Yield

Conditions & References With mercury(II) diacetate Moehrle,H.; Schittenhelm,D.; Chemische Berichte; vol. 104; (1971); p. 2475 - 2482 View in Reaxys O

N O

Brâ&#x20AC;&#x201C;

+Mg

O

Rx-ID: 179046 View in Reaxys 145/182 Yield

Conditions & References With diethyl ether, Erwaermen des Reaktionsprodukts mit wss. HCl Cuvigny; Annales de Chimie (Cachan, France); vol. <13> 1; (1956); p. 475,489 View in Reaxys O

O

Rx-ID: 265862 View in Reaxys 146/182 Yield

Conditions & References With mercury(II) diacetate, anschliessend Behandeln mit Wasser Gaudemar; Annales de Chimie (Cachan, France); vol. <13>1; (1956); p. 161,184,186 View in Reaxys Bourguel; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 192; (1931); p. 686 View in Reaxys With air Bourguel; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 192; (1931); p. 686 View in Reaxys O

phenacyl alcohol

O

Rx-ID: 6163029 View in Reaxys 147/182 Yield

Conditions & References With methanol, formaldehyd, lead(II) hydroxide on calcium carbonate, Erwaermen des Reaktionsprodukts mit wss. H2SO4 Krueger; Chemische Berichte; vol. 89; (1956); p. 1016,1018 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

Br–

+Mg

O

Rx-ID: 22147468 View in Reaxys 148/182 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether / -15 °C 2: mercury (II)-acetate / anschliessend Behandeln mit Wasser With diethyl ether, mercury(II) diacetate Gaudemar; Annales de Chimie (Cachan, France); vol. <13>1; (1956); p. 161,184,186 View in Reaxys O

O N HO

O

Rx-ID: 281756 View in Reaxys 149/182 Yield

Conditions & References With steam, sulfuric acid Hartman; Roll; ; vol. Vol. III; (1955); p. 20 View in Reaxys O

O O

O N

O O

Rx-ID: 343637 View in Reaxys 150/182 Yield

Conditions & References With piperidine, diethyl ether Emmons; Freeman; Journal of the American Chemical Society; vol. 77; (1955); p. 4415 View in Reaxys

O

Cl

H

O

N

O

N

Rx-ID: 5711639 View in Reaxys 151/182 Yield

Conditions & References Beim mehrtaegigen Behandeln Williams; Day; Journal of the American Chemical Society; vol. 74; (1952); p. 3875 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

O

O

Rx-ID: 724609 View in Reaxys 152/182 Yield

Conditions & References With ethanol, sulfuric acid, mercury(II) sulfate Bowden; Braude; Jones; Journal of the Chemical Society; (1946); p. 948 View in Reaxys O O

O O Se

O

O

O

Rx-ID: 6163027 View in Reaxys 153/182 Yield

Conditions & References Wegmann; Dahn; Helvetica Chimica Acta; vol. 29; (1946); p. 1247,1249 View in Reaxys O

O (v1)

OH

O

Hg 2+

S OO

HO

O

-2

(v1)

ethanolic solution

S OO

O

Rx-ID: 6163028 View in Reaxys 154/182 Yield

Conditions & References Bowden; Braude; Jones; Journal of the Chemical Society; (1946); p. 948 View in Reaxys O

aq.-ethanolic Na2CO3-solution

Cl

O

O HO

2-hydroxy-1-phenyl-propanone-(1)

H

O

Rx-ID: 7065627 View in Reaxys 155/182 Yield

Conditions & References Richard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 214; (1942); p. 673 View in Reaxys

Cl

O

aq.-ethanolic Na2CO3-solution

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1-Phenyl-1,2-propanedione [C9H8O2]

O

2-hydroxy-1-phenyl-propanone-(1)

O

1-hydroxy-1-phenyl-propanone-(2)

Rx-ID: 7448937 View in Reaxys 156/182 Yield

Conditions & References Richard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 214; (1942); p. 673 View in Reaxys O O

O

–O

O

O

OH

Na +

HO

O

Cl

O

Rx-ID: 638772 View in Reaxys 157/182 Yield

Conditions & References Bradley; Eaton; Journal of the Chemical Society; (1937); p. 1913 View in Reaxys O

(+-)-3-chloro-1-acetoxy-1-phenyl-acetone

O

Rx-ID: 6163023 View in Reaxys 158/182 Yield

Conditions & References With sodium acetate, acetic acid Bradley; Eaton; Journal of the Chemical Society; (1937); p. 1913 View in Reaxys HO Cl

(v4)

O

O

O

O

O O

O

O O

HO

Rx-ID: 6684562 View in Reaxys 159/182 Yield

Conditions & References Weygand; Koch; Schaecher; Chemische Berichte; vol. 68; (1935); p. 234,239 View in Reaxys Cl

O

KO H

O

O O O

O HO

Rx-ID: 7449442 View in Reaxys 160/182 Yield

Conditions & References Richard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 200; (1935); p. 1944

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1-Phenyl-1,2-propanedione [C9H8O2]

View in Reaxys

OH

O

H

O HO

H

O

Rx-ID: 782371 View in Reaxys 161/182 Yield

Conditions & References With water, mercury(II) sulfate Faworskii <Favorsky>; Temnikowa; Zhurnal Obshchei Khimii; vol. 4; (1934); p. 745,753; Bulletin de la Societe Chimique de France; vol. <5> 2; (1935); p. 253,262 View in Reaxys With water, mercury(II) sulfate, zuletzt unter Erwaermen Faworskii <Favorsky>; Temnikowa; Zhurnal Obshchei Khimii; vol. 4; (1934); p. 745,753; Bulletin de la Societe Chimique de France; vol. <5> 2; (1935); p. 253,262 View in Reaxys

O

O

OH -2

H

(v1)

H

O

H Hg 2+

O

S (v1)

O

O O

HO

H

O

Rx-ID: 6163032 View in Reaxys 162/182 Yield

Conditions & References zuletzt unter Erwaermen auf dem Dampfbad Faworskii <Favorsky>; Temnikowa; Zhurnal Obshchei Khimii; vol. 4; (1934); p. 745,753; Bulletin de la Societe Chimique de France; vol. <5> 2; (1935); p. 253,262 View in Reaxys O

O OH

O Se

O

O

Rx-ID: 6163025 View in Reaxys 163/182 Yield

Conditions & References Riley; Morley; Friend; Journal of the Chemical Society; (1932); p. 1875,1880 View in Reaxys O –

O

2

O

O Hg 2+

Rx-ID: 265860 View in Reaxys 164/182 Yield

Conditions & References Bourguel; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 192; (1931); p. 686 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

Gaudemar; Annales de Chimie (Cachan, France); vol. <13> 1; p. 186,187 View in Reaxys O

(+-)-2-azido-1-phenyl-propanone-(1)

O

Rx-ID: 6163022 View in Reaxys 165/182 Yield

Conditions & References With hydrogenchloride Patent; Knoll A.G.; DE573722; (1931); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 19; p. 1474 View in Reaxys O

air

O

Rx-ID: 7065626 View in Reaxys 166/182 Yield

Conditions & References Bourguel; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 192; (1931); p. 686 View in Reaxys

O OH

OH HO

O

S OO

OH

HO

O

H

O

Rx-ID: 8263494 View in Reaxys 167/182 Yield

Conditions & References T= 135 °C Danilow; Venus-Danilowa; Chemische Berichte; vol. 63; (1930); p. 2765,2774; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 62; (1930); p. 1697,1710 View in Reaxys

O

(+-)-2-hydroxy-3-phenyl-propionaldehyde

O HO

H

O

Rx-ID: 8263495 View in Reaxys 168/182 Yield

Conditions & References With ethanol, sulfuric acid, T= 135 °C Danilow; Venus-Danilowa; Chemische Berichte; vol. 63; (1930); p. 2765,2774; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 62; (1930); p. 1697,1710 View in Reaxys O

O

Cl

H

N O

O

N

calcium chloride O

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1-Phenyl-1,2-propanedione [C9H8O2]

O O

O HO

Rx-ID: 6163035 View in Reaxys 169/182 Yield

Conditions & References T= 60 °C Coles; Manske; Johnson; Journal of the American Chemical Society; vol. 51; (1929); p. 2271 View in Reaxys O O

O

Rx-ID: 753110 View in Reaxys 170/182 Yield

Conditions & References With piperidine, bromine, Kochen des Reaktionsprodukts mit Schwefelsaeure Dufraisse; Moureu; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 184; (1927); p. 99; Bulletin de la Societe Chimique de France; vol. <4>41; (1927); p. 1375 View in Reaxys With diethyl ether, diethylamine, Kochen des Reaktionsprodukts mit Schwefelsaeure Dufraisse; Moureu; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 184; (1927); p. 99; Bulletin de la Societe Chimique de France; vol. <4>41; (1927); p. 1375 View in Reaxys O

O Br

Br

O

O

Rx-ID: 6163026 View in Reaxys 171/182 Yield

Conditions & References aufeinanderfolgend Einw. von Piperidin oder Diaethylamin und Kochen des Reaktionsprodukts mit Schwefelsaeure Dufraisse; Moureu; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 184; (1927); p. 99; Bulletin de la Societe Chimique de France; vol. <4>41; (1927); p. 1375 View in Reaxys O

phenylacetylcarbinol

O

Rx-ID: 6163030 View in Reaxys 172/182 Yield

Conditions & References With copper, T= 350 °C Mailhe; Bulletin de la Societe Chimique de France; vol. <4>15; (1914); p. 328 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

copper HO

O

H

O

Rx-ID: 6684561 View in Reaxys 173/182 Yield

Conditions & References T= 350 °C Mailhe; Bulletin de la Societe Chimique de France; vol. <4>15; (1914); p. 328 View in Reaxys

O

O N

OH O

H

O

OH

HO

H

Rx-ID: 8263493 View in Reaxys 174/182 Yield

Conditions & References Zincke; Zahn; Chemische Berichte; vol. 43; (1910); p. 855 View in Reaxys O

O

Br

α-oxy-propiophenone; propiophenone

O

Rx-ID: 6163031 View in Reaxys 175/182 Yield

Conditions & References With potassium hydroxide Kohler; American Chemical Journal; vol. 41; (1909); p. 425 View in Reaxys O

O

O

alcoholic potash

Br

O

Rx-ID: 6163034 View in Reaxys 176/182 Yield

Conditions & References Kohler; American Chemical Journal; vol. 41; (1909); p. 425 View in Reaxys

OH

O

N N N

O

N OH

Rx-ID: 510334 View in Reaxys 177/182 Yield

Conditions & References With sulfuric acid

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1-Phenyl-1,2-propanedione [C9H8O2]

Ponzio; Giovetti; Gazzetta Chimica Italiana; vol. 38 II; (1908); p. 125 View in Reaxys

OH O

N OH HO

N N

S OO

O

N OH

Rx-ID: 8263492 View in Reaxys 178/182 Yield

Conditions & References Ponzio; Giovetti; Gazzetta Chimica Italiana; vol. 38 II; (1908); p. 125 View in Reaxys HO

O

N

OH HO

S OO

O

O

Rx-ID: 6163024 View in Reaxys 179/182 Yield

Conditions & References Kolb; Justus Liebigs Annalen der Chemie; vol. 291; (1896); p. 267 View in Reaxys Borsche; Chemische Berichte; vol. 40; (1907); p. 743 View in Reaxys O

N

N+

O

Rx-ID: 22032796 View in Reaxys 180/182 Yield

Conditions & References Reaction Steps: 2 1: NaOH-solution 2: sulfuric acid / beim Destillieren With sodium hydroxide, sulfuric acid Borsche; Chemische Berichte; vol. 40; (1907); p. 743 View in Reaxys HO

N

O

O N

N

O

O O

O

O

phenyldinitromethane

O

Rx-ID: 6218360 View in Reaxys 181/182 Yield

Conditions & References T= 0 °C Ponzio; Gazzetta Chimica Italiana; vol. 31 II; (1901); p. 135,136 View in Reaxys

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1-Phenyl-1,2-propanedione [C9H8O2]

O

O N HO

H 2N

diluted acid

OH

O

Rx-ID: 6163033 View in Reaxys 182/182 Yield

Conditions & References bei der Destillation v. Pechmann; Mueller; Chemische Berichte; vol. 21; (1888); p. 2119 View in Reaxys

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