Benzoyl peroxide (Dibenzoyl peroxide) [C14H10O4]

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47 reactions in Reaxys

2018-02-22 00h:00m:27s (EST)

O O

1. Query

O O

Search as: As drawn AND (IDE.XRN=984320)

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O

O O

Cl

O

O

Rx-ID: 616114 View in Reaxys 1/47 Yield 93 %

Conditions & References With sodium hydroxide, dihydrogen peroxide in 1,1,2-Trichloro-1,2,2-trifluoroethane, T= 0 - 5 °C Rakhimov, A. I.; Androsyuk, E. R.; Shelyazhenko, S. V.; Yagupol'skii, L. M.; Journal of Organic Chemistry USSR (English Translation); (1981); p. 1470 - 1475; Zhurnal Organicheskoi Khimii; vol. 17; nb. 8; (1981); p. 1652 - 1657 View in Reaxys With dihydrogen peroxide, sodium carbonate Patent; McKee; DE540588; (1926); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 478 View in Reaxys With sodium peroxide Schwyzer,J.; View in Reaxys With sodium peroxide Nencki; Zaleski; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 27; (1899); p. 493 View in Reaxys With barium peroxide Brodie; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1863); p.

317 View in Reaxys Brodie; Journal of the Chemical Society; vol. 17; (1864); p. 269; ; vol. 121; (1864); p. 377 View in Reaxys With sodium hydroxide, dihydrogen peroxide Baeyer; Villiger; Chemische Berichte; vol. 33; (1900); p. 1581 View in Reaxys v. Pechmann; Vanino; Chemische Berichte; vol. 27; (1894); p. 1511 View in Reaxys With (2S)-N-methyl-1-phenylpropan-2-amine hydrate, sodium peroxide, acetone Gambarjan; Chemische Berichte; vol. 42; (1909); p. 4010 View in Reaxys With barium peroxide, water Orndorff; White; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 12; (1893); p. 68 View in Reaxys Sonnenschein; Monatshefte fuer Chemie; vol. 7; (1886); p. 522 Anm. View in Reaxys With sodium peroxide, water, T= 0 °C Prileshajew; Zhurnal Russkago Fiziko-Khimicheskago Obshchestva; vol. 42; (1910); p. 1409; Chem. Zentralbl.; vol.

82; nb. I; (1911); p. 1280 View in Reaxys Nencki; Zaleski; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 27; (1899); p. 493 View in Reaxys With sodium hydroxide, dihydrogen peroxide

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D'Ans et al.; Angewandte Chemie; vol. 65; (1953); p. 57 View in Reaxys 1 : 4.1 Preparation of benzoyl peroxide analogs 15 General procedure: Benzoyl peroxide analogs were prepared according to literature procedure.

Sodium hydroxide (1.75 g) and 15 mL water were added into a round-bottom flask, 2.0 mL hydrogen peroxide and 0.025 g sodium dodecyl sulfate were added dropwise at 0 °C, 0.013 mol benzoyl chloride analogs were added dropwise slowly under stirring.

The reaction mixture was allowed to stir an additional 2.5 h.

White solid could be obtained in this reaction.

The solid was filtered out and washed with methanol/water (1:1).

Then, it was placed in vacuum oven to dry 24 h.

With dihydrogen peroxide, sodium dodecyl-sulfate, sodium hydroxide in water, Time= 2.5h, T= 0 °C Chen, Huan-Huan; Wang, Guang-Zu; Han, Jin; Xu, Meng-Yu; Zhao, Yong-Qiang; Xu, Hua-Jian; Tetrahedron; vol. 70; nb. 2; (2014); p. 212 - 217 View in Reaxys 54 kg

2 :The method for synthesizing peroxybenzoyl provided by the present embodiment comprises, in particular, the following steps:S21, 150 g of sodium dodecyl sulfate was dissolved in 120 kg of water at room temperature, stirred for 30 minutes, and then 18.5 kg of sodium hydroxide was added to stir to dissolve to obtain a solution which kept the solution temperature between -5 and 5 ° C, And add 24kg mass fraction of 30percent hydrogen peroxide, drop after the completion of insulation and stirring for 1 hour, to be fully reacted, the sodium peroxide solution;S22, the temperature of the sodium peroxide solution is maintained between -5 and 5 ° C, and then 50 kg of benzoyl chloride is added dropwise. After completion of the dropwise addition, the mixture is allowed to warm and stirred for 1 hour. The solution after the reaction is centrifuged, and the centrifuged solid And washed with water to obtain 54 kg of benzoyl peroxide product.

With dihydrogen peroxide, sodium dodecyl-sulfate, sodium hydroxide in water, Time= 2.5h, T= -5 - 5 °C , Heating, Large scale, Concentration, Solvent, Reagent/catalyst Patent; jiangsu wanchuan healthcare industry group co ltd; Liu, Hui; Wang, Peng; Chen, Zailing; Sun, Jue; (9 pag.); CN105924378; (2016); (A) Chinese View in Reaxys

14.1 kg

2 : Example 2 (1) synthetic process:A. 22 kg of 30percent hydrogen peroxide was added to a 50 L reactor,Open the stir,Then add 13.5 kg of ammonium bicarbonate,15 kg of benzoyl chloride was slowly added dropwise,The temperature inside the reactor is 30 degrees Celsius,Reaction time is 3.5 hours;B. The reaction solution was filtered and filtered to obtain a filter cake. The filter cake was beaten and washed in a mixed solvent of 30 kg of ethanol and 30 kg of water for 40 minutes,C. Wash with 45kg of water for 20 minutes, repeated beating washing 3 times;. D finally rinsed with 45kg of water, drained, benzoyl peroxide to give a crude white; (2) purification process:E. Add the crude benzoyl benzoate into a 200 L autoclave, add 52.5 kg of dichloromethane to the autoclave, control the temperature inside the autoclave at 30 ° C, stir to dissolve;F. 105kg of ethanol pressure filter to the high position, room temperature drop of ethanol, open the cooling, the reaction solution temperature dropped to -5 degrees Celsius, cooling crystallization 2.5 hours;G. After the crystallization is complete, the filter is filtered and the filter cake is removed and beaten with water for 20 minutes.Repeated beating washing 3 times,And finally 14.1 kg of white high purity benzoyl peroxide was obtained.The purity of benzoyl peroxide prepared in this example was 99.5percent.

With dihydrogen peroxide, ammonium bicarbonate, Time= 3.5h, T= 30 °C , Large scale, Temperature Patent; Jiangsu Sinobiopharma Co., Ltd.; Huang, Lequn; Chen, Quan; (6 pag.); CN106349139; (2017); (A) Chinese View in Reaxys

Cl

SH

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O S Cl

O

O

Cl

S

O

Cl

S O

O

O

Rx-ID: 45977436 View in Reaxys 2/47 Yield

Conditions & References With eosin Y disodium salt in acetonitrile, Time= 24h, Irradiation Štrukil, Vjekoslav; Sajko, Igor; Chemical Communications; vol. 53; nb. 65; (2017); p. 9101 - 9104 View in Reaxys

O O

O

O

Rx-ID: 6718970 View in Reaxys 3/47 Yield 70.0%

Conditions & References 2 : Example 2 Example 2 A benzoyl peroxide in cocoa butter composition is prepared.

Cocoa butter (4.0 g) and Tween 20 (12 mL) and deionized water (235 mL) are added together and heated to 40-45° C. with overhead stirring.

The mixture is stirred for 1 h.

Then benzoyl peroxide (25.0 g, 74.6percent by wt) is added portionwise to the cocoa butter solution.

The mixture is allowed to stir at 40-45° C. for 45 minutes then at ambient temperature overnight.

After stirring, the mixture is allowed to stand for 1 h.

Then the aqueous layer is decanted away.

The solids are filtered and dried, resulting in a white solid (21.4 g, 70.0percent benzoyl peroxide retention).

The solids are analyzed by HPLC to determine the solids contain approximately 60.6percent benzoyl peroxide (by weight).

Patent; Norac Pharma; US2012/64135; (2012); (A1) English View in Reaxys

56%

9.b : b. b.

Use of benzoyl peroxide as the initiator A mixture of 1.0 g (7.93 mmol) of 3,4-dihydro-4,4-dimethyl-2H-pyran-2-one and 6.29 g (31.7 mmol) of bromotrichloromethane was heated to 100° C. Heating was maintained at 100° C. for 12 hours.

During this time 600 mg (2.48 mmol) of benzoyl peroxide was added in six 100 mg portions; a 100 mg portion being added approximately every 2 hours.

The reaction mixture was cooled and placed on a silica gel packed chromatography column.

Elution with 20:1 hexane:ethyl acetate mixture afforded 1.45 g, 56percent yield, of 5-bromo-3,4,5,6-tetrahydro-3,3dimethyl-6-trichloromethyl-2H-pyran-2-one.

Patent; FMC Corporation; US4235780; (1980); (A1) English View in Reaxys Staab,H.A. et al.; Chemische Berichte; vol. 98; (1965); p. 1122 - 1127 View in Reaxys Staab et al.; Chemische Berichte; vol. 98; (1965); p. 1128,1132 View in Reaxys Staab; Angewandte Chemie; vol. 74; (1962); p. 407,417 View in Reaxys Ramirez et al.; Journal of the American Chemical Society; vol. 82; (1960); p. 5763 View in Reaxys Le Berre; Berguer; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 260; (1965); p. 1995 View in Reaxys

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Patent; Koppers Co.; GB1156573; (1967); ; vol. 71; nb. 61023x; (1969) View in Reaxys Patent; Pfizer; Chas and Co.; Inc.; US3438882; (1964); ; vol. 71; nb. 12843f; (1969) View in Reaxys Berre; Bergue; Bulletin de la Societe Chimique de France; (1966); p. 2368,2373 View in Reaxys Ol'dekop et al.; Journal of Organic Chemistry USSR (English Translation); vol. 2; (1966); p. 2133; Zhurnal Organicheskoi Khimii; vol. 2; (1966); p. 2175 View in Reaxys Ivanov; Bagira; J. Appl. Chem. USSR (Engl. Transl.); vol. 48; (1975); p. 243,243 View in Reaxys Johnson; Tetrahedron Letters; (1976); p. 331 View in Reaxys Otsuka et al.; Journal of the American Chemical Society; vol. 94; (1972); p. 3761,3767 View in Reaxys Greene; Kazan; Journal of Organic Chemistry; vol. 28; (1963); p. 2168,2169 View in Reaxys Ol'dekop; El'nizkii; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 3478,3520 View in Reaxys Voronkov et al.; Soobshcheniya Akademii Nauk Gruzinskoi SSR; vol. 93; nb. 1; (1979); p. 61,62,63,64 View in Reaxys Sprecher; Nativ; Tetrahedron Letters; (1968); p. 4405 View in Reaxys 3 : EXAMPLE 3 EXAMPLE 3 The following benzoyl peroxide creamy wash is prepared in accordance with the procedures set forth in Example 1.

The lactic acid is added along with the glycolic acid.

Patent; Popp, Karl F.; Stiefel, Brent D.; US6433024; (2002); (B1) English View in Reaxys 4 : EXAMPLE 4 EXAMPLE 4 The following benzoyl peroxide creamy wash is prepared in accordance with the procedures set forth in Example 1.

The lactic acid is added at the point were the glyolic acid is added in Example 1.

Patent; Popp, Karl F.; Stiefel, Brent D.; US6433024; (2002); (B1) English View in Reaxys 6 : Example 6 Example 6 A reactor equipped with a reflux condenser, a stirrer, a dropping funnel and a thermometer was charged with 100 g of xylene and the system was purged with nitrogen.

Separately, a mixed solution comprising 150 g of butyl acrylate, 5 g of methacrylic acid, 15 g of the resin reforming agent of the present invention: (1-b), (5-b), (11)-(15), (17-b), (22-b) or (26), or the comparative compound (1)-(3), 2 g of benzoyl peroxide, and 0.5 g of di-tertiary butyl peroxide was prepared and it was continuously added to the reactor dropwise at a reaction temperature of 130° C. over a period of 2 hours.

Patent; Asahi Denka Kogyo K. K.; US5929290; (1999); (A1) English View in Reaxys 1 : EXAMPLE 1 EXAMPLE 1 An initial charge containing 2.1 g t-octyl acrylamide, 16.76 g butyl acrylate, 5.0 g vinyl acetate, 1.0 g acrylic acid, 39.9 g ethyl acetate (solvent) and 0.04 g benzoyl peroxide (polymerization initiator) was prepared and charged to a 1-liter four-neck round bottom flask equipped with stainless steel stirrer, thermometer, condenser, water bath, slow addition funnels.

Patent; National Starch and Chemical Investment Holding Corporation; EP913445; (1999); (A1) English View in Reaxys 2 : Example 2 Example 2

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In the same manner as in Example 1 except that 0.3 part by weight of dibenzoyl peroxide was used instead of 0.2 part by weight thereof, a patch was prepared.

Patent; Nitto Denko Corporation; US2010/15210; (2010); (A1) English View in Reaxys 3 : Example 3 Example 3 In the same manner as in Example 1 except that 0.35 part by weight of dibenzoyl peroxide was used instead of 0.2 part by weight thereof, a patch was prepared.

Patent; Nitto Denko Corporation; US2010/15210; (2010); (A1) English View in Reaxys 4 : Example 4 Example 4 In the same manner as in Example 1 except that 0.4 part by weight of dibenzoyl peroxide was used instead of 0.2 part by weight thereof, a patch was prepared.

Patent; Nitto Denko Corporation; US2010/15210; (2010); (A1) English View in Reaxys 6 : Example 6 Example 6 In the same manner as in Example 5 except that 0.4 part by weight of dibenzoyl peroxide was used instead of 0.3 part by weight thereof, a patch was prepared.

Patent; Nitto Denko Corporation; US2010/15210; (2010); (A1) English View in Reaxys C.1 : Comparative Example 1 Comparative Example 1 In the same manner as in Example 10 except that 0 part by weight of dibenzoyl peroxide was used instead of 0.2 part by weight thereof, a patch was prepared.

Patent; Nitto Denko Corporation; US2010/15210; (2010); (A1) English View in Reaxys C.2 : Comparative Example 2 Comparative Example 2 In the same manner as in Example 10 except that 60 parts by weight of polybutadiene was used instead of polybutadiene and 1 part by weight of dibenzoyl peroxide was used instead of 0.2 part by weight thereof, a patch was prepared.

Patent; Nitto Denko Corporation; US2010/15210; (2010); (A1) English View in Reaxys

O E

E

E

O

E

O

OH

O

O

Rx-ID: 32645926 View in Reaxys 4/47 Yield

Conditions & References 8 : Example 8 Example 8 A benzoyl peroxide and tretinoin in cocoa butter melt is prepared.

Cocoa butter (1.7 g) is stirred at 40-45° C. for 20 minutes.

Benzoyl peroxide (5.0 g, 74.6percent by wt) is introduced and the melt is mixed for an additional 20 min, followed by tretinoin (1.3 g) and the melt is stirred for 30 min at 40° C. The mixture is allowed to cool.

The solids are allowed to air dry which results in an off-white solid (8.0 g).

With dibenzoyl peroxide

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Patent; Norac Pharma; US2012/64135; (2012); (A1) English View in Reaxys

S

O

N

O

O

O

O

O

Rx-ID: 32645927 View in Reaxys 5/47 Yield

Conditions & References 7 : Example 7 Example 7 A benzoyl peroxide and tazarotene in cocoa butter melt is prepared.

Cocoa butter (1.7 g) is stirred at 40-45° C. for 20 minutes.

Benzoyl peroxide (5.0 g, 74.6percent by wt) is introduced and the melt is mixed for an additional 20 min, followed by tazarotene (3.3 g) and the melt is stirred for 30 min at 40° C. The mixture is allowed to cool.

The solids are allowed to air dry which results in an off-white solid (10.0 g).

With dibenzoyl peroxide Patent; Norac Pharma; US2012/64135; (2012); (A1) English View in Reaxys

O

O

Cl

Cl

O

O O

O

O

O

O O

O

O

O

O

Rx-ID: 9324887 View in Reaxys 6/47 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide, trimethyloctadecylammonium chloride in butanone, Time= 0.5h, T= 15 °C , Title compound not separated from byproducts Moorhoff, Cornelis M.; Braybrook, Carl; Journal of Chemical Research, Miniprint; nb. 3; (2003); p. 339 - 361 View in Reaxys

O

O

Cl

Cl

O

O O

O

O

O

O O

O

O

O

O

Rx-ID: 9324889 View in Reaxys 7/47 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide, trimethyloctadecylammonium chloride in butanone, Time= 0.5h, T= 15 °C , Title compound not separated from byproducts Moorhoff, Cornelis M.; Braybrook, Carl; Journal of Chemical Research, Miniprint; nb. 3; (2003); p. 339 - 361 View in Reaxys

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O

O

O

Cl

O

O O

O

O

Cl

O O

O

O

O

O

Rx-ID: 9324935 View in Reaxys 8/47 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide, trimethyloctadecylammonium chloride in butanone, Time= 0.5h, T= 15 °C , Title compound not separated from byproducts Moorhoff, Cornelis M.; Braybrook, Carl; Journal of Chemical Research, Miniprint; nb. 3; (2003); p. 339 - 361 View in Reaxys

O

O

Cl

Cl

O O

O O

O

O O

O

O

O

O

O

Rx-ID: 9325003 View in Reaxys 9/47 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide, trimethyloctadecylammonium chloride, ortho-toluoyl chloride in butanone, Time= 0.5h, T= 15 °C , Title compound not separated from byproducts Moorhoff, Cornelis M.; Braybrook, Carl; Journal of Chemical Research, Miniprint; nb. 3; (2003); p. 339 - 361 View in Reaxys

O O

O

O

Rx-ID: 24274928 View in Reaxys 10/47 Yield

Conditions & References 5 : Example 5 Example 5 A reactor equipped with a reflux condenser, a stirrer, a dropping funnel and a thermometer was charged with 100 g of xylene and the system was purged with nitrogen.

Separately, a mixed solution comprising of 150 g of styrene, 7.5 g of the resin reforming agent of the present invention: (1-b), (5-b), (11)-(15), (17-b), (22-b), or (26), or the comparative compound (1)-(3), 2 g of benzoyl peroxide, and 1 g of di-tertiary butyl peroxide was prepared and continuously added to the reactor dropwise at a reaction temperature of 130° C. over a period of 2 hours. in 5,5-dimethyl-1,3-cyclohexadiene Patent; Asahi Denka Kogyo K. K.; US5929290; (1999); (A1) English View in Reaxys

F

Cl F

O

O O

Cl

O

O

Rx-ID: 24719659 View in Reaxys 11/47 Yield

Conditions & References 53.A : Ultrasonic Batch Reaction of Benzoyl Chloride A.

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Giving Benzoyl Peroxide as Major Product: A beaker was loaded with 1.23 g ~85percent KOH pellets (19 mmoles) dissolved up to 15.9 ml with water, 2.04 ml of 30percent aqueous hydrogen peroxide (20 mmoles), 50 ml of Freon.(R). E1, and 2.32 ml of benzoyl chloride (20 mmoles) with ice bath cooling.

An ultrasonic horn connected to a 40 Khz, 150 watt Dukane power source was started up at maximum power and lowered into the reaction mixture.

After 25 seconds, ultrasonication was stopped, the solids filtered off, washed with water, and sucked dry on the filter.

This gave 1.52 g of white solid, a 63percent yield of benzoyl peroxide based on starting benzoyl chloride.

The filtrate was brought to pH ~1 by the addition of concentrated sulfuric acid and then extracted three times with methylene chloride.

The three methylene chloride extracts had a combined volume of 80 ml, 10.0 ml of which took 0.2 ml of 0.1N thiosulfate in iodometric peroxide titration.

The failure to find significant amounts of peroxide in the methylene chloride extracts indicates that little if any benzoyl hydroperoxide C6 H5 (C=O)OOH! was formed during the reaction.

With potassium hydroxide, dihydrogen peroxide Patent; E. I. du Pont de Nemours and Company; US5831131; (1998); (A1) English View in Reaxys

O O

O

OH

O

O

Rx-ID: 24989968 View in Reaxys 12/47 Yield

Conditions & References Paste A Quartz treated with γ-methacryloxypropyl trimethoxysilane (50 μm or less): 67.5 parts by weight Benzoyl peroxide: 1.5 parts by weight Hydroquinone monomethyl ether: 0.01 part by weight Patent; G-C Dental Industrial Corporation; US4713403; (1987); (A1) English View in Reaxys 2H

2H

O 2H

HO

2H

O 2H

2H

2H

2H

2H

2H

O

O

O 2H

2H

O

O

HO 2H

2H

2H

O

O

2H

Rx-ID: 1701148 View in Reaxys 13/47 Yield

Conditions & References With cobalt(III) acetylacetonate, T= 25 °C , Mechanism, Product distribution Lederer, Pavel; Macova, Eva; Veprek-Siska, Josef; Collection of Czechoslovak Chemical Communications; vol.

49; nb. 3; (1984); p. 673 - 679 View in Reaxys

O HO

O

O O

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O

O O

HO

product X 4percent,

O

O

Rx-ID: 6730988 View in Reaxys 14/47 Yield 6 %, 8 %, 90 %, 2 %

Conditions & References With cobalt(III) acetylacetonate, Time= 5h, T= 24.9 °C , Ea; other metal 2,4-pentandioates (Co(II), Fe(III), Mn(III), Cr(III))., Mechanism, Product distribution, Thermodynamic data Lederer, Pavel; Macova, Eva; Veprek-Siska, Josef; Collection of Czechoslovak Chemical Communications; vol.

49; nb. 3; (1984); p. 673 - 679 View in Reaxys

O

O O

13C

Cl

O

O

Rx-ID: 2064785 View in Reaxys 15/47 Yield

Conditions & References With sodium peroxide Takeuchi, Ken'ichi; Murai, Osamu; Matsui, Shin; Inoue, Takeshi; Kitagawa, Toshikazu; Okamoto, Kunio; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1983); p. 1301 1310 View in Reaxys

H

O

O

O O

O

HO

HO

O

O

O

Rx-ID: 2690873 View in Reaxys 16/47 Yield 83.2 %

Conditions & References With oxygen, ozone, lithium chloride in tetrachloromethane, T= 40 °C El'nitskii, A. P.; Serrano, K. F.; Poluyan, O. S.; Journal of Organic Chemistry USSR (English Translation); vol. 19; nb. 8; (1983); p. 1565 - 1566; Zhurnal Organicheskoi Khimii; vol. 19; nb. 8; (1983); p. 1764 View in Reaxys

O

O O

13

C

HO

O

O

Rx-ID: 20867517 View in Reaxys 17/47 Yield

Conditions & References Reaction Steps: 2 1: SOCl2 2: Na2O2 With thionyl chloride, sodium peroxide Takeuchi, Ken'ichi; Murai, Osamu; Matsui, Shin; Inoue, Takeshi; Kitagawa, Toshikazu; Okamoto, Kunio; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 9; (1983); p. 1301 1310 View in Reaxys

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10/18

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O

O O

O

O

O

O

Rx-ID: 674373 View in Reaxys 18/47 Yield

Conditions & References With barium peroxide Brodie; Journal of the Chemical Society; vol. 17; (1864); p. 269; ; vol. 121; (1864); p. 377 View in Reaxys With potassium hydroxide, dihydrogen peroxide Clover; Richmond; American Chemical Journal; vol. 29; (1903); p. 189 View in Reaxys

9 % Chromat.

With dioxygenbis(triphenylphosphine)platinum(0) in dichloromethane, Time= 2h Aida, Shun'ichi; Ohta, Hiroyuki; Kamiya, Yoshio; Chemistry Letters; (1981); p. 1639 - 1642 View in Reaxys

O

O O

HO

O

O

Rx-ID: 3552637 View in Reaxys 19/47 Yield

Conditions & References

90 %

With dihydrogen peroxide, dicyclohexyl-carbodiimide in diethyl ether, dichloromethane, Time= 2h, T= 0 °C , Mechanism Rakhimov, A. I.; Androsyuk, E. R.; Shelyazhenko, S. V.; Yagupol'skii, L. M.; Journal of Organic Chemistry USSR (English Translation); (1981); p. 1470 - 1475; Zhurnal Organicheskoi Khimii; vol. 17; nb. 8; (1981); p. 1652 - 1657 View in Reaxys

90 %

With dihydrogen peroxide, dicyclohexyl-carbodiimide in diethyl ether, dichloromethane, T= 0 - 2 °C Rakhimov, A. I.; Androsyuk, E. R.; Shelyazhenko, S. V.; Yagupol'skii, L. M.; Journal of Organic Chemistry USSR (English Translation); (1981); p. 1470 - 1475; Zhurnal Organicheskoi Khimii; vol. 17; nb. 8; (1981); p. 1652 - 1657 View in Reaxys

O

PtBr<OOC(O)Ph>(PPh3)2

Br

O

O O

O

O

cis-PtBr2(PPh3)2

O

O

Rx-ID: 6211530 View in Reaxys 20/47 Yield 27 %, 22 %

Conditions & References in dichloromethane, Time= 6h, T= -78 °C Tatsuno, Y.; Otsuka, Sei; Journal of the American Chemical Society; vol. 103; nb. 19; (1981); p. 5832 - 5839 View in Reaxys

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O

O O

O

O

O

Rx-ID: 20703930 View in Reaxys 21/47 Yield

Conditions & References Reaction Steps: 2 1: 55 percent Chromat. / peroxobis(triphenylphosphine)platinum(II) / CH2Cl2 / 28 h 2: 9 percent Chromat. / peroxobis(triphenylphosphine)platinum(II) / CH2Cl2 / 2 h With dioxygenbis(triphenylphosphine)platinum(0) in dichloromethane Aida, Shun'ichi; Ohta, Hiroyuki; Kamiya, Yoshio; Chemistry Letters; (1981); p. 1639 - 1642 View in Reaxys

(v3)

N

2

O

(v4)

N

(v4)

C

(v4)

Ni

Br O

O

(v4)

N

Ni

Br

O

O

N

O

O

Br

Rx-ID: 26623716 View in Reaxys 22/47 Yield

Conditions & References in dichloromethane, -70°C Otsuka, S.; Nakamura, A.; Tatsuno, Y.; Mike, M.; Journal of the American Chemical Society; vol. 94; (1972); p.

3761 - 3767 ; (from Gmelin) View in Reaxys in dichloromethane, -70°C vol. Ni: Org.Verb.2; 7, page 393 - 402 ; (from Gmelin) View in Reaxys

(v3)

N

2

O

O

(v4)

Ni

O

C

N

Cl O

O

O

O

Rx-ID: 26629723 View in Reaxys 23/47 Yield

Conditions & References in toluene, -10°C Otsuka, S.; Nakamura, A.; Tatsuno, Y.; Mike, M.; Journal of the American Chemical Society; vol. 94; (1972); p.

3761 - 3767 ; (from Gmelin) View in Reaxys in toluene, -10°C vol. Ni: Org.Verb.2; 7, page 393 - 402 ; (from Gmelin) View in Reaxys

O

O

O

O

Br Br

O

O

O

Rx-ID: 29052 View in Reaxys 24/47 Yield

Conditions & References With tetrachloromethane, N-Bromosuccinimide, Erwaermen des Reaktionsprodukts mit Natriumaethylat in Aethanol und Aether

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Paul; Tchelitcheff; Bulletin de la Societe Chimique de France; (1956); p. 869,874 View in Reaxys

O

HO

O

O

O O

O

S Cl

O

O

Rx-ID: 729467 View in Reaxys 25/47 Yield

Conditions & References T= 0 °C Kirmse; Horner; Chemische Berichte; vol. 89; (1956); p. 836,840 View in Reaxys

O

O

Br HO

O

Br

O

O

O

Rx-ID: 6718971 View in Reaxys 26/47 Yield

Conditions & References T= 20 °C Kirmse; Horner; Chemische Berichte; vol. 89; (1956); p. 836,840 View in Reaxys

O

O

Cl HO

O

Cl

O

O

O

Rx-ID: 6718972 View in Reaxys 27/47 Yield

Conditions & References T= 25 °C Kirmse; Horner; Chemische Berichte; vol. 89; (1956); p. 836,840 View in Reaxys

Cl

Cl

Cl

Cl

H

ozone containing oxygen O

O

O O

HO

O

O

Rx-ID: 5721497 View in Reaxys 28/47 Yield

Conditions & References T= 0 °C Marvel; Nichols; Journal of Organic Chemistry; vol. 6; (1941); p. 296,299 View in Reaxys

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HO

O

O

P O HO H

Cl

O O

O

O

Rx-ID: 26453213 View in Reaxys 29/47 Yield

Conditions & References With NaOH or pyridine in water, an aq. soln. of peroxophosphorous acid, from O3- or F2O-induced autoxid-ation of aq. H3PO3, treated with NaOH or pyridine, is forming dibenzoyl-peroxide with benzoylchloride; Bockemueller, W.; Goetz, T.; Liebigs Annalen der Chemie; vol. 508; (1934); p. 263 - 297 View in Reaxys vol. P: MVol.C; 64, page 136 - 138 ; (from Gmelin) View in Reaxys

O

O HO

O

O

OH

O

aqueous NaOH-solution Cl

O

O

Rx-ID: 7067430 View in Reaxys 30/47 Yield

Conditions & References Fenton; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 90; (1914); p. 493; Chem. Zentralbl.; vol. 85; nb. II; (1914); p. 863 View in Reaxys

O

O H

O

H

O

sodium peroxide Cl

O

O

Rx-ID: 6208710 View in Reaxys 31/47 Yield

Conditions & References Gambarjan; Chemische Berichte; vol. 42; (1909); p. 4010 View in Reaxys Nencki; Zaleski; Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie; vol. 27; (1899); p. 493 View in Reaxys

O O

O

O

O

O

O

O

Rx-ID: 283131 View in Reaxys 32/47 Yield

Conditions & References With sodium carbonate, T= 50 °C Jorissen; Ringer; Journal fuer Praktische Chemie (Leipzig); vol. <2> 72; (1905); p. 173; Chem. Zentralbl.; vol. 76; nb. I; (1905); p. 817 View in Reaxys Jorissen; Ringer; Chem. Zentralbl.; vol. 76; nb. I; (1905); p. 817 View in Reaxys

O O

O

O

O

O

natrium carbonate

O

O

Rx-ID: 7450195 View in Reaxys 33/47

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Yield

Conditions & References T= 50 °C Baeyer; Villiger; Chemische Berichte; vol. 33; (1900); p. 1581 View in Reaxys Nef; Justus Liebigs Annalen der Chemie; vol. 298; (1897); p. 322; Justus Liebigs Annalen der Chemie; vol. 318; (1901); p. 50 View in Reaxys Jorissen; Ringer; Journal fuer Praktische Chemie (Leipzig); vol. <2> 72; (1905); p. 173; Chem. Zentralbl.; vol. 76; nb. I; (1905); p. 817 View in Reaxys Jorissen; Ringer; Chem. Zentralbl.; vol. 76; nb. I; (1905); p. 817 View in Reaxys

O

H O

O

O

O

Rx-ID: 22021698 View in Reaxys 34/47 Yield

Conditions & References Reaction Steps: 2 1: sand; air 2: natrium carbonate / 50 °C With air, sodium carbonate Jorissen; Ringer; Journal fuer Praktische Chemie (Leipzig); vol. <2> 72; (1905); p. 173; Chem. Zentralbl.; vol. 76; nb. I; (1905); p. 817 View in Reaxys Jorissen; Ringer; Chem. Zentralbl.; vol. 76; nb. I; (1905); p. 817 View in Reaxys

O

O

O

–O

OH

O

O

O

Na +

O

O

O

O

Cl

O

O

Rx-ID: 609400 View in Reaxys 35/47 Yield

Conditions & References Clover; Richmond; American Chemical Journal; vol. 29; (1903); p. 189 View in Reaxys

O

O O

O O

O

HO

O

O

O

Rx-ID: 674374 View in Reaxys 36/47 Yield

Conditions & References With potassium hydroxide, dihydrogen peroxide, T= 0 °C Clover; Richmond; American Chemical Journal; vol. 29; (1903); p. 189 View in Reaxys O

H

O

O

H

O O

potassium hydroxide

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15/18

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O

O O

HO

O

O

O

Rx-ID: 6208711 View in Reaxys 37/47 Yield

Conditions & References T= 0 °C Clover; Richmond; American Chemical Journal; vol. 29; (1903); p. 189 View in Reaxys

–O

O

O Na +

acetyl hydrogen peroxide Cl

O O

O

O

O

O

O

O

Rx-ID: 6208712 View in Reaxys 38/47 Yield

Conditions & References Clover; Richmond; American Chemical Journal; vol. 29; (1903); p. 189 View in Reaxys

O

O

O

acetyl hydrogen peroxide

O

O

O

O

Cl

O

O

Rx-ID: 7450196 View in Reaxys 39/47 Yield

Conditions & References With water, sodium acetate Clover; Richmond; American Chemical Journal; vol. 29; (1903); p. 189 View in Reaxys

O

O

O O

HO

O

Cl

O

O

Rx-ID: 609482 View in Reaxys 40/47 Yield

Conditions & References With sodium hydrogencarbonate Baeyer; Villiger; Chemische Berichte; vol. 33; (1900); p. 1581 View in Reaxys

O

O

O O

sodium bicarbonate HO

O

Cl

O

O

Rx-ID: 6208709 View in Reaxys 41/47 Yield

Conditions & References Baeyer; Villiger; Chemische Berichte; vol. 33; (1900); p. 1581 View in Reaxys

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16/18

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Na + –O

O

O

O

O

Na +

air

O–

O

O

O

Rx-ID: 8265576 View in Reaxys 42/47 Yield

Conditions & References Baeyer; Villiger; Chemische Berichte; vol. 33; (1900); p. 1581 View in Reaxys O

O

O

O

diluted NaOH-solution

O

O O

HO

sodium peroxide

O

oxygen

O

Rx-ID: 7457918 View in Reaxys 43/47 Yield

Conditions & References Nef; Justus Liebigs Annalen der Chemie; vol. 298; (1897); p. 322; Justus Liebigs Annalen der Chemie; vol. 318; (1901); p. 50 View in Reaxys

O O H

O

O

O

N O

H

O

O

Cl

O

O

O

Rx-ID: 6208705 View in Reaxys 44/47 Yield

Conditions & References v. Pechmann; Vanino; Chemische Berichte; vol. 27; (1894); p. 1511 View in Reaxys T= -5 °C v. Pechmann; Vanino; Chemische Berichte; vol. 27; (1894); p. 1511 View in Reaxys

O

O H

O

H

O

barium peroxide hydrate Cl

O

O

Rx-ID: 6208707 View in Reaxys 45/47 Yield

Conditions & References Orndorff; White; Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre; vol. 12; (1893); p. 68 View in Reaxys Sonnenschein; Monatshefte fuer Chemie; vol. 7; (1886); p. 522 Anm. View in Reaxys

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17/18

2018-02-22 00:16:19

O

O O

barium peroxide hydrate Cl

O

O

Rx-ID: 6208706 View in Reaxys 46/47 Yield

Conditions & References Brodie; Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften; (1863); p.

317 View in Reaxys Brodie; Journal of the Chemical Society; vol. 17; (1864); p. 269; ; vol. 121; (1864); p. 377 View in Reaxys

O

O O

O

O

barium peroxide hydrate

O

O

Rx-ID: 6208708 View in Reaxys 47/47 Yield

Conditions & References Brodie; Journal of the Chemical Society; vol. 17; (1864); p. 269; ; vol. 121; (1864); p. 377 View in Reaxys

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18/18

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