2-Phenylpropan-2-ol by Asch

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487 reactions in Reaxys

2016-05-12 15h:55m:27s (EST)

487 reactions in Reaxys

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O Br Mg

Rx-ID: 4579516 View in Reaxys 1/487 Yield 75 %

Conditions & References 4 :4. Reaction of phenylmagnesium bromide with acetone in trihexvKtetradecyl) phosphonium chloride; [00059] To dried ionic liquid trihexyl(tetradecyl) phosphonium chloride (15 .bul.mL), 1 M phenylmagnesium bromide solution in tetrahydrofuran (5.00 mL, 5.00 mmol) was added. To this stirred solution acetone (0.29 g, 5.00 mmol) was added dropwise and allowed to stir for 3 hours and quenched under nitrogen with saturated ammonium chloride followed by water. Hexanes were added to extract 2-phenyl-propan-2-ol and the hexanes extract after drying with anhydrous magnesium sulphate and ionic liquid layer were analyzed by GC-MS giving a total yield of 82percent. Distillation under vacuum was also carried out giving a yield of 75 percent. Stage 1: in Cyphos® IL 101, tetrahydrofuran, Time= 3h Stage 2: With ammonium chloride in Cyphos® IL 101, tetrahydrofuran, water Patent; SIMON FRASER UNIVERSITY; WO2006/7703; (2006); (A1) English View in Reaxys in diethyl ether, Ambient temperature Lomas, John S.; Journal of the Chemical Society. Perkin Transactions 2; vol. 1996; nb. 12; (1996); p. 2601 - 2609 View in Reaxys in diethyl ether, Time= 1h, Ambient temperature Aelterman, Wim; Tehrani, Kourosch Abbaspour; Coppens, Wim; Huybrechts, Tom; De Kimpe, Norbert; Tourwe, Dirk; Declercq, Jean-Paul; European Journal of Organic Chemistry; nb. 1; (1999); p. 239 - 250 View in Reaxys

70 %Chromat.

2 : Example 2 Preparation of α,α-dimethylbenzyl alcohol using CPME as a reaction solvent Example 2 Preparation of α,α-dimethylbenzyl alcohol using CPME as a reaction solvent 45 ml (0.045 mol) of a 1 M phenylmagnesium bromide (PhMgBr) solution in THF was added to a flask, of which the atmosphere had been replaced with nitrogen, and stirred at 0°C for 30 minutes.. A solution of 1.74 g (0.03 mol) of acetone in 50 ml of CPME was slowly added dropwise to the PhMgBr solution at 0°C. After stirring at 0°C for one hour, the reacted mixture was heated to 50°C and stirred for a further one hour.. The reaction mixture was allowed to cool to room temperature and 20 ml of 1 N hydrochloric acid aqueous solution was added to terminate the reaction.. The reaction mixture was analyzed by gas chromatography to confirm that the target α,α-dimethylbenzyl alcohol was obtained in a yield of 70percent. in tetrahydrofuran, CPME, Time= 2.5h, T= 0 - 50 °C Patent; Zeon Corporation; EP1405840; (2004); (A1) English View in Reaxys

85 %Chromat.

22-23 : Example 22 Synthesis of α,α-dimethylbenzyl alcohol using Solvent A 40 parts of a 1 M phenylmagnesium bromide (PhMgBr) solution in Solvent A was added to a flask, of which the atmosphere has been replaced with nitrogen, and stirred at 0°C for 30 minutes. A solution of 1.74 parts of acetone in 70 parts of Solvent A was slowly added dropwise to the PhMgBr solution at 0°C. After stirring at 0°C for one hour, the reaction mixture was heated to 50°C and stirred for a further one hour. After cooling to room temperature, the reaction was terminated with the addition of 20 parts of 1 N hydrochloric acid aqueous solution. The reaction mixture was analyzed by gas chromatography to confirm that the target α,α-dimethylbenzyl alcohol was obtained in a yield of 85percent. 50 parts of water was added to partition the mixture into two layers. The organic layer was removed and distilled under atmospheric pressure using a Vigreux rectification column to obtain 99 parts of fractions distilled at 100-106°C. Gas chromatography analysis confirmed that the distillate contained 99percent or more of CPME. The distillate can be used again as a solvent. in CPME, Time= 2.5h, T= 0 - 50 °C Patent; Zeon Corporation; EP1405840; (2004); (A1) English View in Reaxys

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Rx-ID: 281381 View in Reaxys 2/487 Yield 100 %

Conditions & References With di-p-methoxyphenyl telluride in pyridine, acetic acid, Time= 0.166667h, Ambient temperature Barton; Csuhai; Ozbalik; Tetrahedron Letters; vol. 31; nb. 20; (1990); p. 2717 - 2820 View in Reaxys

100 %

With 1,3,5-triphenylverdazyl radical in benzene, T= 20 °C , Eap, Rate constant, Thermodynamic data Buzulukov, V. I.; Zhivechkova, L. A.; Russian Journal of General Chemistry; vol. 64; nb. 2; (1994); p. 276 - 278; Zhurnal Obshchei Khimii; vol. 64; nb. 2; (1994); p. 306 - 308 View in Reaxys

72 %

With phenyl silane, oxygen, Co(modp)2 in 1,2-dichloro-ethane, Time= 4h, T= 20 °C Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys With sodium hydroxide, Electrolysis Patent; Hercules Powder Co.; US2543763; (1949) View in Reaxys With methanol, nickel, Hydrogenation Patent; Hercules Powder Co.; US2491926; (1947) View in Reaxys With aluminum oxide, palladium/alumina, Hydrogenation Patent; Distillers Co.; US2854487; (1956) View in Reaxys With water, tin(ll) chloride Patent; Hercules Powder Co.; US2557968; (1948) View in Reaxys With chromium dichloride, water Patent; Hercules Powder Co.; US2557968; (1948) View in Reaxys With sodium sulfide Patent; Hercules Powder Co.; US2484841; (1947) View in Reaxys With methanol, platinum, Hydrogenation Patent; Hercules Powder Co.; US2491926; (1947) View in Reaxys With 2-isopropyl-1,3-dioxolane in chlorobenzene, Time= 1h, T= 130 °C , presence of inhibitor, Rate constant Kuramshin, E. M.; Molyavko, M. A.; Zlot-skii, S. S.; Rakhmankulov, D. L.; J. Gen. Chem. USSR (Engl. Transl.); vol. 55; nb. 6; (1985); p. 1393 - 1398,1242 - 1246 View in Reaxys With potassium hydroxide, phenylacetylene in N,N,N',N',N'',N''-hexamethylphosphoric triamide, T= 343 °C , decomposition in superbasic medium Lyavinets; Choban; Chervinskii; Russian Journal of General Chemistry; vol. 68; nb. 7; (1998); p. 1116 - 1119

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View in Reaxys With tetrabutylammomium bromide in water, Time= 1h, T= 80 °C Matsunaka, Katsuhisa; Iwahama, Takahiro; Sakaguchi, Satoshi; Ishii, Yasutaka; Tetrahedron Letters; vol. 40; nb. 11; (1999); p. 2165 - 2168 View in Reaxys With 2,6-di-tert-butyl-4-methyl-phenol, triphenylphosphine in benzene Pratt, Derek A.; Mills, Jeremy H.; Porter, Ned A.; Journal of the American Chemical Society; vol. 125; nb. 19; (2003); p. 5801 - 5810 View in Reaxys With triphenylphosphine in acetonitrile, T= 25 °C Fukuda, Osamu; Sakaguchi, Satoshi; Ishii, Yasutaka; Advanced Synthesis and Catalysis; vol. 343; nb. 8; (2001); p. 809 - 813 View in Reaxys Reaction Steps: 2 1: 23 percent / triethylamine / hexane / 10 h / 0 °C 2: 38 percent / silica gel / diethyl ether; hexane With silica gel, triethylamine in diethyl ether, hexane Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys 2 : EXAMPLE 2 [0037] To a 250-ml round bottom flask fitted with a condenser, stirrer and dropping funnel, and located in a water bath for temperature control, was charged a mixture of 100.0 g of acetone and 1.00 g of the catalyst of Example 1. The mixture was heated to reflux (57° C.) with stirring, and 50.0 g of 80 wt.percent CHP solution (analyzed as 80.8 wt.percent CHP, 7.7 wt.percent cumene, 6.9 wt.percent DMPC, 2.1 wt.percent acetophenone) was added dropwise at an approximate rate of 2 g/min. Following addition of the CHP solution, small samples (0.2 ml) of the reactant solution were withdrawn at regular intervals, filtered, and analyzed by gas chromatograph (GC). [0038] Table II below shows the composition (wt.percent) of the reactant solution at 1 and 3 hours after the addition of the CHP was complete. For analyzing the data in Table II, the following definitions are provided: [0039] CHP Conversion (percent)=(wt.percent CHPfeed-wt.percent CHPproduct)/(wt.percent CHPfeed) [0040] percent Increase in DMPC=(wt.percent DMPCproduct-wt.percent DMPCfeed)/(wt.percent DMPCfeed) [TABLE-US-00002] TABLE II Feed 1 hr 3 hr Acetone 66.67 66.97 66.72 Cumene 2.56 2.41 2.31 Phenol 0.09 0.05 0.06 α-Methyl Styrene 0.07 0.15 0.16 Acetophenone 0.70 1.57 1.97 DMPC 2.36 5.95 7.67 Cumene Hydroperoxide 26.93 22.53 20.71 CHP Conversion 16.4percent 23.1percent percent Increase in DMPC 152.4percent 225.2percent [0041] The above example shows that the Co/Al/PO4 catalyst reduces the CHP to DMPC. The catalyst, being non-acidic, is inactive for the decomposition of CHP into phenol and acetone. With Co/Al/PO4 catalyst, T= 57 °C Patent; Levin, Doron; Smith, C. Morris; Santiesteban, Jose Guadalupe; Vartuli, James C.; US2004/116749; (2004); (A1) English View in Reaxys 4 : EXAMPLE 4 [0043] To a 250-ml round bottom flask fitted with a condenser, stirrer and dropping funnel, and located in a water bath for temperature control, was charged a mixture of 100.0 g of acetone and 1.00 g of the catalyst of Example 3. The mixture was heated to reflux (57° C.) with stirring, and 50.0 g of 80 wt.percent CHP solution (analyzed as 80.8 wt.percent CHP, 7.7 wt.percent cumene, 6.9 wt.percent DMPC, 2.1 wt.percent acetophenone) was added dropwise at an approximate rate of 2 g/min. Following addition of the CHP solution, small samples (0.2 ml) of the reactant solution were withdrawn at regular intervals, filtered, and analyzed by GC. [0044] Table III below shows the composition (wt.percent) of the reactant solution at 1 and 3 hours after the addition of the CHP was complete. [TABLEUS-00003] TABLE III Feed 1 hr 3 hr Acetone 66.67 67.37 67.32 Cumene 2.56 2.27 2.20 Phenol 0.09 0.04 0.03 αMethyl Styrene 0.07 0.13 0.13 Acetophenone 0.70 2.29 2.43 DMPC 2.36 8.52 9.95 Cumene Hydroperoxide 26.93 19.17 17.48 CHP Conversion 28.8percent 35.1percent percent Increase in DMPC 261.2percent 321.9percent [0045] The above example shows that a Co/ZrO2 catalyst reduces the CHP to DMPC. The catalyst, being non-acidic, is inactive for the decomposition of CHP into phenol and acetone.

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, T= 57 °C Patent; Levin, Doron; Smith, C. Morris; Santiesteban, Jose Guadalupe; Vartuli, James C.; US2004/116749; (2004); (A1) English View in Reaxys 4 :Cumene hydroperoxide was dissolved in ethanol at room temperature to give a solution containing 1.035percentw/w hydroperoxide. The reactor set- up comprised of a T-mixer and a subsequent capillary-reactor with an internal diameter of 0.53mm and a length of 0.50m. The capillary reactor had a fused silica wall that was coated with a 6 micron porous alumina layer. This alumina layer contained palladium crystallites (11nm) as catalytic active material. The T-mixer and reactant pump were at room temperature. The capillary-reactor was placed in a waterbath at 220C. Cumene hydroperoxide solution was pumped into the T-mixer with a flow of 0.250 ml/min. Hydrogen gas was fed into the T-mixer with a flow of 0.600 ml/min (1 bar). The T-mixer produced a taylor flow regime (liquid slugs). The product coming out of the reactor was collected. Samples were analysed with GC and HPLC. A conversion of 73percent with >99percent selectivity was obtained towards 2-phenyl-2-propanol. See Figure 4. With hydrogen, palladium/alumina in ethanol, T= 20 °C , p= 750.075Torr Patent; DSM IP ASSETS B.V.; WO2007/134847; (2007); (A2) English View in Reaxys With C20H28N2O2Se2, thiophenol in methanol, T= 22 °C Bhabak, Krishna P.; Mugesh, Govindasamy; Chemistry - A European Journal; vol. 14; nb. 28; (2008); p. 8640 8651 View in Reaxys 100 1 :Example 2: Sulfuric Acid Catalyzed Cleavage of Dilute Cumene Hydroperoxide (CHP) [0082] Cumene oxidation %Chromat. products (including cumeme hyroperoxide, CHP) from Example 1 where NHPI was used as the first catalyst was used (containing 19.8percent CHP, 77.6percent cumene, 1.1percent acetophenone, and 0.9percent cumyl alcohol). An amount of 5.0 milliliters of such feed was charged into a glass flask held at 54°C. To this feed was added 0.5 milliliters of 1.5 wt.percent sulfuric acid in nitromethane, giving a sulfuric acid concentration of 1600 ppm. Cleavage reaction occurred instantaneously as indicated by the reaction exotherm. An aliquot was taken after 15 min and sulfuric acid was neutralized using 10 wt.percent sodium carbonate solution. The sample was analyzed by GC. Complete conversions for CHP and cumyl alcohol were achieved and only a small amount (0.6 wt.percent) of heavy product cumyl phenol (alkylation products of α-methylstyrene with phenol) was observed. With sulfuric acid in nitromethane Patent; EXXONMOBIL CHEMICAL PATENTS INC.; WANG, Kun; BENITEZ, Francisco, M.; LATTNER, James, R.; DAKKA, Jihad, M.; MOZELESKI, Edmund, J.; ZUSHMA, Stephen; WO2010/98916; (2010); (A2) English View in Reaxys With 3-mercapto-6-nitro-benzoic acid, T= 25 °C , pH= 7, aq. phosphate buffer, Kinetics, Reagent/catalyst Tang, Yong; Zhou, Lipeng; Li, Jiaxi; Luo, Quan; Huang, Xin; Wu, Ping; Wang, Yongguo; Xu, Jiayun; Shen, Jiacong; Liu, Junqiu; Angewandte Chemie - International Edition; vol. 49; nb. 23; (2010); p. 3920 - 3924 View in Reaxys 2 :Example 2 - Oxidation of cumene; A solution composed of 400 mL of cumene (2,870 mmoles) , 150 mL of acetonitrile and 28.7 mmoles (4.7 g) of N-hydroxyphthalimide is stirred at 60 °C for 6 hours in an oxygen atmosphere at a pressure of 1 bar. 1H-NMR analysis of the reaction mixture showed a conversion of cumene equal to 35percent with a selectivity to cumyl hydroperoxide of 99percent (result confirmed through iodometric titration, GC-MS analysis in the presence of an internal standard after reduction of the hydroperoxide to the corresponding alcohol with PPh3 and HPLC analysis of the reaction mixture without any treatment. With triphenylphosphine Patent; POLIMERI EUROPA S.P.A.; RECUPERO, Francesco; PUNTA, Carlo; MELONE, Lucio; PROSPERINI, Simona; PASTORI, Nadia; WO2011/161523; (2011); (A1) English View in Reaxys 1 :[Examples 1 and 2] Alpha methyl styrene was prepared according to the process flow diagram ofFig. 2. First, oxidation of cumene was progressed with an oxidizer under the following conditions using 3 oxidation reactors in a phenol process to prepare a stream including cumene hydroperoxide (CHP) of concentration of 25 wtpercent. (1) Condi-

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tion of introducing first oxidizer supply (CHP 0.4percent + cumene 99.6percent) 1 ml/min, 02: 100 ml/min, pressure: 3bar, reaction temperature: 100 °C (2) Condition of introducing second oxidizer supply (CHP 8.42percent + cumene 91.58percent) 1 ml/min, 02: 100 ml/min, pressure:3bar, reaction temperature: 96 °C (3) Condition of introducing third oxidizer supply (CHP 16.27percent + cumene 83.73percent) 1 ml/min, 02: 100 ml/min, pressure: 3bar, reaction temperature: 94 °C The concentration of CHP stream was changed from 8.4 to 24 wtpercent while passing through 3 oxidation reactors as shown in the following Table 1. Then, 25 wtpercent of the stream of low concentration was separated and transferred to a receiver (20), and then, supplied to a catalytic hydrogenation reactor (30). The hydrogenation reactor was filled with a catalyst Pd/C, hydrogen was introduced and the reaction was progressed while maintaining internal temperature. And, the reactant of cumene hydroperoxide stream of 25 wtpercent concentration was introduced top-down of the reactor using a pressurization pump. The hydrogenation reaction was progressed under conditions of 150 g of cumene hydroperoxide (CHP) of 25 wtpercent concentration, 1 g of 1 wtpercent Pd/C, and hydrogen flow rate of 150 cc/min. And, the mole ratio of the cumene hydroperoxide stream and the introduced hydrogen was maintained 1 :8. The hydrogen reaction was progressed respectively for 7 hours and 3 hours in Examples 1 and 2. As the result, final product with cumene hydroperoxide (CHP) conversion rate of 99.97percent, CA increase rate of 960.5percent, and CA concentration of 25percent was obtained. After the reaction was completed, conversion rate of cumene hydroperoxied into cumyl alcohol was analyzed with liquid chromatography, and the result was shown in Table 2. After the hydrogenation reaction is completed, prepared cumyl alcohol is supplied to the receiver (20), and transferred to the stripper (40). Thereby, the stripper (40) is filled with a mixture of cumyl alcohol obtained by the hydrogenation reaction, and a stream including cumyl alcohol and cumene hydroperoxide which are not used in the hydrogen reaction. Then, the mixture is concentrated in the stripper (40), passed through a receiver (50) and transferred to a cleavage reactor (60), and the remainder is directly transferred to the cleavage reactor. And then, an acid catalyst is introduced in the cleavage reactor (60), and the mixture is continuously dehydrated so that the acid catalyst decomposes cumene hydroperoxide into phenol and acetone, and dehydrates cumyl alcohol into AMS. Into the cleavage reactor, 100 g of feedstock (CHP 72 wtpercent, CA 8 wtpercent, cumene 20 wtpercent) and 1 g of H2S04 were introduced to progress the reaction. And, the reaction temperature was maintained 65 °C , and raised to 1 10°C after conversion until the concentration of CHP became less than 1percent, so as to convert CA into AMS. The mixture of phenol, acetone and AMS produced in the cleavage reactor (60) was transferred to a neutralizer reactor (70), and a neutralization agent was introduced to progress a neutralization reaction. After neutralization, the product was transferred to a distillation reactor (80), and separated into phenol, AMS and acetone through distillation. By the above reaction, yield for conversion from CHP into phenol was 99.36percent, yield for conversion from CHP into aceton was 98.30percent, and yield for conversion from CA into AMS was 82.45percent. [Table 1 ]The above Table 1 shows that most of CHP was decomposed into phenol and acetone and the concentration decreased from 82 wtpercent to 1 wtpercent in the 1st cleavage reactor, and 1 wtpercent of CHP decreased to 1 wtpercent or less in the 2nd cleavage reactor. With hydrogen, palladium on activated charcoal, Time= 7h, T= 65 °C , Product distribution / selectivity Patent; LG CHEM, LTD.; HA, Seung-Back; YOO, Suk-Joon; CHO, Dong-Hyun; WO2012/74194; (2012); (A2) English View in Reaxys

I O

Rx-ID: 715527 View in Reaxys 3/487 Yield 93 %

Conditions & References Stage 1: With trimethylsilyl-methylmagnesium chloride, lithium chloride, zinc(II) chloride in tetrahydrofuran, diethyl ether, T= 20 °C , Grignard addition Stage 2: in tetrahydrofuran, diethyl ether, Time= 3h, T= 0 °C , Grignard addition Hatano, Manabu; Ito, Orie; Suzuki, Shinji; Ishihara, Kazuaki; Chemical Communications; vol. 46; nb. 15; (2010); p. 2674 - 2676 View in Reaxys

93 %

Stage 1: With trimethylsilyl-methylmagnesium chloride, lithium chloride, zinc(II) chloride in tetrahydrofuran, diethyl ether, Time= 0.75h, T= 20 °C , Inert atmosphere Stage 2: in tetrahydrofuran, diethyl ether, Time= 3h, T= 0 °C , Inert atmosphere Hatano, Manabu; Ito, Orie; Suzuki, Shinji; Ishihara, Kazuaki; Journal of Organic Chemistry; vol. 75; nb. 15; (2010); p. 5008 - 5016 View in Reaxys

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70 %

Villenave, J. J.; Filliatre, C.; Maillard, B.; Jaouhari, R.; Bulletin des Societes Chimiques Belges; vol. 91; nb. 4; (1982); p. 301 - 310 View in Reaxys Grignard; Annales de Chimie (Cachan, France); vol. <7> 24; (1901); p. 468; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys Klages; Chemische Berichte; vol. 35; (1902); p. 2649; Chemische Berichte; vol. 39; (1906); p. 2591 View in Reaxys Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 130; (1900); p. 1324; Annales de Chimie (Cachan, France); vol. <7>24; (1901); p. 472; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys Liu, Kwang-Ting; Wu, Yuh Wern; Tetrahedron Letters; vol. 27; nb. 31; (1986); p. 3623 - 3626 View in Reaxys in diethyl ether, Grignard reaction Thomas; Asokan; Journal of the Chemical Society. Perkin Transactions 1; nb. 20; (2001); p. 2583 - 2587 View in Reaxys in diethyl ether Peppe, Clovis; Lang, Ernesto Schulz; De Andrade, Fabiano Molinos; De Castro, Lierson Borges; Synlett; nb. 10; (2004); p. 1723 - 1726 View in Reaxys

Rx-ID: 1709977 View in Reaxys 4/487 Yield 38.0 %, 0.28 %, 2.24 %

Conditions & References With oxygen, phen, zinc pyrazolonate, Time= 5h, T= 110 °C , effect of further monodentate and bidentate activators, Product distribution Kozlov; Tovstokhat'ko; Potekhin; Journal of applied chemistry of the USSR; vol. 59; nb. 6 pt 2; (1986); p. 1287 1290 View in Reaxys

20.02 %

Comparative example-oxidation catalyzed by NaOH; The reactor was charged with 250g of cumene containing a percentage of about 1-2percent of cumene hydroperoxide. 280 mg of a 50percent NaOH solution were also charged to the reactor. The reaction was run under stirring at 112°C and at a pressure of 5 atm, while feeding an air flow (contaning about 20percent of oxygen) of 15 Nl/hour. The reaction was extended for 240 minutes, until reaching a cumene conversion of 24. 5percent. The analysis of the cumene hydroperoxide thus obtained (a colorless product) evidenced, after removing the cumene by distillation, the following main byproducts content (per 100 g of cumene hydroperoxide): dimethylphenylcarbinol** 3. 75 g acetophenone** 0.39 g sodium cation* 1.64 mg * determined by atomic absorption ** determined by HPLC technique A hydroperoxide yield of 20. 02percent and a selectivity of 81. 74percent was calculated. With sodium hydroxide, oxygen in water, Time= 4h, T= 112 °C , p= 3800.26Torr , Industry scale, Product distribution / selectivity Patent; EUROTECNICA DEVELOPMENT and LICENSING S.P.A.; WO2003/76381; (2003); (A1) English View in Reaxys

20.43 %

Example of the invention process-oxidation in the presence of pyridinic resins; The reactor was charged with 250 g of cumene containing a cumene hydroperoxide percentage of about 1- 2percent. The reactor was also charged with 6 g of REILLEX 402 resin. The reaction was performed under agitation at 112°C and at a pressure of 5 atm, while feeding a flow of air (containing about 20percent of oxygen) at 10 Nl/hour. The reaction was extended for 360 minutes, up to a cumene conversion of 22.12percent. The analysis of the cumene hydroperoxide thus obtained (a colorless product) evidenced, after removing the cumene by distillation, the following main byproducts content (per 100 g of cumene hydroperoxide): dimethylphenylcarbinol** 1. 5 g acetophenone** 0.21 g sodium cation* untraceable * determined by atomic absorption ** determined by HPLC technique A hydroperoxide yield of 20. 43percent and a selectivity of 92. 39percent was calculated.

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With oxygen, REILLEX.(TM). 402 resin, Time= 6h, T= 112 °C , p= 3800.26Torr , Industry scale, Product distribution / selectivity Patent; EUROTECNICA DEVELOPMENT and LICENSING S.P.A.; WO2003/76381; (2003); (A1) English View in Reaxys 11.5 %, 10.8 %, 3.6 %

With oxygen, Co3(DBM)3(pz)4(OH)*2THF in chlorobenzene, T= 74.85 °C , Product distribution

14 % Spectr., 8 % Spectr., 9% Spectr.

With oxygen, ammonium cerium(IV) nitrate in acetonitrile, Time= 5h, Ambient temperature, Irradiation, Title compound not separated from byproducts

Lukasiewicz, Marta; Ciunik, Zbigniew; Mazurek, Jaroslaw; Sobczak, Jaroslaw; Staron, Aldona; Wolowiec, Stanislaw; Ziolkowski, Jozef J.; European Journal of Inorganic Chemistry; nb. 6; (2001); p. 1575 - 1579 View in Reaxys

Baciocchi, E.; Giacco, T. Del; Sebastiani, G. V.; Rol, C.; Tetrahedron Letters; vol. 26; nb. 28; (1985); p. 3353 3356 View in Reaxys With oxygen, phen, Time= 4h, T= 110 °C , different catalytic systems and reaction times, Product distribution Kozlov; Tovstokhat'ko; Potekhin; Journal of applied chemistry of the USSR; vol. 59; nb. 1 pt 2; (1986); p. 205 207 View in Reaxys

9% Spectr., 8 % Spectr., 14 % Spectr.

With oxygen, ammonium cerium(IV) nitrate in acetonitrile, Time= 5h, Ambient temperature, Irradiation, Title compound not separated from byproducts

9% Spectr., 14 % Spectr., 8% Spectr.

With oxygen, ammonium cerium(IV) nitrate in acetonitrile, Time= 5h, Ambient temperature, Irradiation, Title compound not separated from byproducts

Baciocchi, E.; Giacco, T. Del; Sebastiani, G. V.; Rol, C.; Tetrahedron Letters; vol. 26; nb. 28; (1985); p. 3353 3356 View in Reaxys

Baciocchi, E.; Giacco, T. Del; Sebastiani, G. V.; Rol, C.; Tetrahedron Letters; vol. 26; nb. 28; (1985); p. 3353 3356 View in Reaxys With air, Cu 18(2), T= 60 °C , Kinetics, Further Variations: Catalysts Skorokhodova; Kobotaeva; Sirotkina; Russian Journal of Applied Chemistry; vol. 78; nb. 5; (2005); p. 753 - 757 View in Reaxys 1-6 : EXAMPLES 1-6 EXAMPLES 1-6; The basic experiment parameters (a pressure of 5 atm and a temperature of 80-120° C.) simulate the working conditions of the individual reactors of an actual industrial plant. The feedstock flow rate was selected in such a manner that the CHP concentration gain corresponded to a six-reactor system. [0044] In the experiments, cumene of a purity of no less than 99.85percent was used. The aqueous phase was prepared from ammonium bicarbonate of the "chemically pure" grade with an ammonia content of no less than 21.7percent. [0045] The oxidative feedstock for each of the experiments was either pure commercial cumene (first reactor, T=120° C.) or oxidation products obtained in the course of the previous experiments. [0046] The concentration of CHP was determined by iodometric titration. [0047] The concentrations of ACP and DMPC were determined by gas-liquid chromatography: a chromatograph with a flame ionization detector and a 25 m long column with an outer diameter of 0.32 mm; stationary liquid phase: OV-1; Tinitial=50° C., temperature rising rate: 8° C./min, Tfinal=20° C. The quantitative calculations were performed using n-pentadecane as the internal standard. [0048] The aqueous phase flowrate was 6-7 ml/hr while the oxidative feedstock flowrate was 200-260 ml/hr. [0049] In order to simulate the operation of an actual sixreactor industrial plant, temperatures falling into the range of 120-87.8° C. were selected (see Table 1). For the first reactor (T=120° C.), pure commercial cumene (CCHP.0=0.07percent) was used as the oxidative feedstock. In the subsequent experiments, the products obtained in the course of the previous experiment were used as feedstock. [0050] The experiments were conducted as follows. In the atmosphere of nitrogen, the reactor was filled, until liquid overflowed into the vessel, with the oxidative feedstock and 20 ml of the 0.001-0.5 mass percent aqueous solution of the ammonium salt and the reactor heating was turned on. After the required temperature was reached, the nitrogen flow was stopped and air feeding was started. In 1 hour, the first sample of the organic phase was taken through a siphon tube and analyzed for CHP content. In another hour, the second sample was taken and sampling was done in

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that manner until the expected CHP concentration was reached. After that, the pumps were turned on and in 12-15 hours the steady mode was established. The aqueous phase was periodically (every 0.5 hours) discharged from the bottom of the reactor. The organic phase was continuously overflowing into a receiving vessel that was discharged periodically. After a steady mode was reached, organic phase samples were taken every 3-4 hours and analyzed for the content of CHP (titration) as well as the contents of DMPC and ACP (gas-liquid chromatography). The duration of each experiment was 24 to 72 hours. [0051] The ammonium salt concentration for each of the experiments was selected experimentally. It has been found that, for each of the simulated reactors, there exists an optimal concentration below which the oxidation reaction rate falls significantly while, at higher concentrations, a decrease in selectivity is observed. With air, ammonia, NH4HCO3 in water, Time= 24 - 72h, T= 80 - 120 °C , p= 3800.26Torr , Conversion of starting material Patent; Dyckman, Arkady Samuilovich; Fulmer, John William; Pinson, Viktor Vladimirovich; Zinenkov, Andrey Vladimirovich; Gorovits, Boris Issakovich; US2004/59162; (2004); (A1) English View in Reaxys 7 : EXAMPLES 7 EXAMPLE 7 [0053] The process is conducted similarly to examples 1-6 but, in oxidation, an aqueous solution of an ammonium salt obtained by passing carbon dioxide gas through an aqueous solution of ammonia is used. At an oxidation temperature of 120° C. and a pressure of 5 atm, the conversion is 5.3percent and the selectivity was 85.7percent. With air, carbon dioxide, ammonia in water, Time= 24 - 72h, T= 80 - 120 °C , p= 3800.26Torr , Conversion of starting material Patent; Dyckman, Arkady Samuilovich; Fulmer, John William; Pinson, Viktor Vladimirovich; Zinenkov, Andrey Vladimirovich; Gorovits, Boris Issakovich; US2004/59162; (2004); (A1) English View in Reaxys 1; 2 :The production of CHP was carried out using three 1 L autoclave type reactor having 100 mm in diameter and 200 mm in hight connected in series. A ring type sparger having 2 mm in diameter of aperture, 10 mm in aperture pitch, and 25 apertures was equipped in each reactor. Raw material comprising 99.0percent by weight of cumene and 1.0percent by weight of CHP was continuously fed to the first reactor at the feed rate of 100 ml/hr. Then oxygencontaining gas having 30 molpercent of oxygen content prepared by mixing 4.96 Nl/hr of air with 0.64 Nl/hr of oxygen in a mixer was fed to each reactor through spargers. Reaction pressure and residence time of each reactor were controlled at 0.4 MPa (gauge pressure) and for 4hrs (total residence time was 12hrs) respectively. Under controlling oxygen content of spent gas of each reactor of 5 molpercent, reaction temperature of the first, the second and the third reactor were 105.5°C, 103.0°C and 102.0°C respectively. While monitoring the composition of the reactant at the outlet of reactor using middle wave infrared spectroscopy, reactant was taken out continuously at a rate of 90g/hr to keep the volume of reaction fluid 400 ml (total volume of reaction fluid was kept 1200 ml). The composition of reactant at the outlet of reactor was shown in Table 1. CHP production was carried out under the condition of oxidizing efficiency and the CHP production per unit volume of the reaction fluid shown in Table 1. Additionally, oxidizing efficiency is calculated using the following equation. Moreover, flow rate of spent gas, leaking rate of cumene to spent gas and leaking rate of oxygen to spent gas are also shown in Table 1. The operation was able to continue stably for two weeks under the above-described conditions.[Show Image][Show Image]Comparative Example 1 The same manner as defined in Example 1 was conducted except that air (21 molpercent of oxygen content) was used as oxygen-containing gas; air was fed at the rate of 8.0Nl/hr to be the same total volume of oxygen as in Example 1; reaction temperatures of the first, the second and the third vessel were adjusted to 104.5°C, 102.0°C and 101.5°C respectively so that the oxygen content of exhaust gas of each reactor is 5 molpercent and reactant was taken out at 88g/hr, to obtain CHP. Table 1 shows the composition of reactant, oxidizing efficiency, CHP production per unit volume of the reaction fluid in the reactor flow rate of spent gas, spent gas flow rate, leaking rate of cumene to spent gas and leaking rate of oxygen to spent gas of this case. Although the stable operation was able to carry out for two weeks under the above-described conditions, CHP production efficiency was inferior to Example 1 due to the decrease of residence time and increase of leaking rate of oxygen to spent gas.Comparative Example 2 The same manner as defined in Example 1 was conducted except that oxygen-containing gas of 60 molpercent of oxygen content which was prepared by mixing air of 1.42Nl/hr with oxygen of 1.38Nl/hr by mixer was fed so that the total volume of oxygen was same as that of Example 1; reaction temperatures of the first, the second and the third reactor were adjusted to 106.0°C, 103.5°C and 103.0°C respectively so that the oxygen content of spent gas of each reactor is 5 molpercent and reactant was taken out at 92g/hr, to obtain CHP. With oxygen, Time= 12h, T= 101.5 - 106 °C , p= 3000.3Torr

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Patent; MITSUBISHI CHEMICAL CORPORATION; EP1721895; (2006); (A1) English View in Reaxys 10.0 % Chromat., 3.5 % Chromat., 1.0 % Chromat.

With oxygen, 1,1'-azobis(1-cyanocyclohexanenitrile) in various solvent(s), Time= 3h, T= 120 °C , Product distribution, Further Variations: Solvents Baj, Stefan; Chrobok, Anna; International Journal of Chemical Kinetics; vol. 40; nb. 6; (2008); p. 287 - 293 View in Reaxys

With copper acetylacetonate, N -hydroxyphthalimide, 2,2'-azobis(isobutyronitrile), oxygen in acetonitrile, Time= 4.5h, T= 60 °C Orlinska, Beata; Tetrahedron Letters; vol. 51; nb. 31; (2010); p. 4100 - 4102 View in Reaxys With N -hydroxyphthalimide, CuCl2·2H2O, oxygen, 1,1'-azobis(1-cyanocyclohexanenitrile) in benzonitrile, Time= 3h, T= 90 °C Orlinska, Beata; Tetrahedron Letters; vol. 51; nb. 31; (2010); p. 4100 - 4102 View in Reaxys With hydrogen peroxide in water, acetonitrile, Time= 24h, T= 80 °C Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys With hydrogen peroxide in water, acetonitrile, Time= 24h, T= 80 °C Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys With 2C3H4N2 (1-)*Cu(2+), oxygen, Time= 23h, T= 80 °C , Catalytic behavior, Reagent/catalyst, Time Luz; Leon; Boronat; Llabres I Xamena; Corma; Catalysis Science and Technology; vol. 3; nb. 2; (2013); p. 371 379 View in Reaxys The liquid oxidation reactions were carried out in a three-necked flask (20 mL), supplied with a magnetic stirrer, refluxcondenser and the oil bath. Cumene (10 mL) and catalyst were put into the flask, sonicated for 5 min, and then heated to preconcertedtemperature followed by the bubbling of oxygen at a constant flowrate. The main product of cumene oxidation is CHP, the by-productsare acetophenone (AP) and 2-benzyl-2-propanol (BP), as shownin Scheme 1. The CHP concentration was determined accordingto the iodometric method [24]. After the reduction of generatedCHP to BP via triphenylphosphine reaction [25], the other prod-ucts in the liquid phase were detected by gas chromatography (anAgilent GC-6820) equipped with a 30 m × 0.25 mm × 0.25 m HP-5capillary column and a flame ionization detector (detector tem-perature 553 K, injector temperature 553 K, and oven temperature413 K) using toluene as external standard. Cumene conversion (X)and products selectivity (S) were calculated using the followingequations (I)–(IV). With oxygen, copper(II) oxide, Time= 8h, T= 79.84 °C , p= 760.051Torr , Reagent/catalyst, Temperature Liao, Shixia; Peng, Feng; Yu, Hao; Wang, Hongjuan; Applied Catalysis A: General; vol. 478; (2014); p. 1 - 8 View in Reaxys

Rx-ID: 67640 View in Reaxys 5/487 Yield 95 %

Conditions & References With sodium tert-pentoxide, sodium hydride, zinc(II) chloride in ethylene glycol dimethyl ether, Time= 1h, T= 65 °C Fort, Yves; Vanderesse, Regis; Caubere, Paul; Tetrahedron Letters; vol. 26; nb. 26; (1985); p. 3111 - 3114 View in Reaxys

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With tetrahydrofuran, lithium aluminium tetrahydride Eliel; Freeman; Journal of the American Chemical Society; vol. 74; (1952); p. 923,925 View in Reaxys 73 % Chromat.

With methanol, sodium tetrahydroborate in tert-butyl alcohol, Time= 1h, Heating Soai, Kenso; Ookawa, Atsuhiro; Oyamada, Hidekazu; Takase, Masako; Heterocycles; vol. 19; nb. 8; (1982); p. 1371 - 1374 View in Reaxys

73 % Spectr.

With sodium tetrahydroborate in methanol, tert-butyl alcohol, Time= 2h Ookawa, Atsuhiro; Hiratsuka, Hiroshi; Soai, Kenso; Bulletin of the Chemical Society of Japan; vol. 60; (1987); p. 1813 - 1818 View in Reaxys

Rx-ID: 108021 View in Reaxys 6/487 Yield 99 %

Conditions & References With N -hydroxyphthalimide, oxygen, [Co(O2CCH3)2]*4H2O in acetonitrile, Time= 9h, T= 40 °C , Kinetics, Solvent Minisci, Francesco; Recupero, Francesco; Cecchetto, Andrea; Gambarotti, Cristian; Punta, Carlo; Paganelli, Roberto; Pedulli, Gian Franco; Fontana, Francesca; Organic Process Research and Development; vol. 8; nb. 2; (2004); p. 163 - 168 View in Reaxys

92 %

With chromium(VI) oxide, tetrabutylammonium (meta)periodate in dichloromethane, acetonitrile, Time= 0.166667h, T= -40 °C Lee, Seongmin; Fuchs; Journal of the American Chemical Society; vol. 124; nb. 47; (2002); p. 13978 - 13979 View in Reaxys

88 %

With potassium permanganate on Y-Zeolite in 1,2-DICHLOROETHANE, Time= 96h, Ambient temperature Sreekumar; Padmakumar, Raghavakaimal; Tetrahedron Letters; vol. 38; nb. 29; (1997); p. 5143 - 5146 View in Reaxys

85 %

in water, Time= 72h, T= 25 °C , by Mortierella isabellina Holland, Herbert L.; Bergen, Eleanor J.; Chenchaiah, P. Chinna; Khan, Shaheer H.; Munoz, Benito; et al.; Canadian Journal of Chemistry; vol. 65; (1987); p. 502 - 507 View in Reaxys

82 %

With potassium permanganate, Tulsion T-42 exchange resin in dichloromethane, tert-butanol, Time= 4h, T= 20 °C , oxidative cleavage Joshi, Padmaker L.; Hazra, Braja G.; Journal of Chemical Research - Part S; nb. 1; (2000); p. 38 - 39 View in Reaxys

78 %

With aluminum oxide, potassium permanganate, water in 1,2-DICHLOROETHANE, Time= 136h, Ambient temperature Zhao; Lee; Synthesis; nb. 9; (1994); p. 915 - 916 View in Reaxys

78 %

With aluminum oxide, potassium permanganate, Time= 136h Noureldin, Nazih A.; Zhao, Dongyuan; Lee, Donald G.; Journal of Organic Chemistry; vol. 62; nb. 25; (1997); p. 8767 - 8772 View in Reaxys

61 %

With potassium permanganate, sulfuric acid, triethylamine in chloroform, Ambient temperature

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Li, Wen-Shan; Liu, Lilian Kao; Synthesis; nb. 4; (1989); p. 293 - 295 View in Reaxys 60 %

With C29H33FeN5O3 (2+)*2CF3O3S(1-) in acetonitrile, Time= 24h Rana, Sujoy; Dey, Aniruddha; Maiti, Debabrata; Chemical Communications; vol. 51; nb. 77; (2015); p. 14469 14472 View in Reaxys

48 %

With [FeIV(O)(2-[bis(pyridin-2-ylmethyl)]amino-N-quinolin-8-yl-acetamido)]ClO4*0.5CH2Cl2 in dichloromethane, acetonitrile, T= 25 °C , Inert atmosphere, Kinetics Hitomi, Yutaka; Arakawa, Kengo; Kodera, Masahito; Chemical Communications; vol. 50; nb. 56; (2014); p. 7485 7487 View in Reaxys

47.5 %

With [Ni(N-methyl-N,N',N'-tris(pyrid-2-ylmethyl)ethylenediamine)(CH3CN)](BPh4)2, m-chloroperbenzoic acid in dichloromethane, acetonitrile, Time= 2h, T= 20 °C , Inert atmosphere, Catalytic behavior, Reagent/catalyst Sankaralingam, Muniyandi; Balamurugan, Mani; Palaniandavar, Mallayan; Vadivelu, Prabha; Suresh, Cherumuttathu H.; Chemistry - A European Journal; vol. 20; nb. 36; (2014); p. 11346 - 11361 View in Reaxys

44 %

With [OsV(O)(2,2’:6’,2’’:6’’,2’’’-quaterpyridine)(4-picoline)Cl](PF6)2 in acetonitrile, T= 23 °C , Inert atmosphere, Kinetics Liu, Yingying; Ng, Siu-Mui; Lam, William W. Y.; Yiu, Shek-Man; Lau, Tai-Chu; Angewandte Chemie - International Edition; vol. 55; nb. 1; (2016); p. 288 - 291; Angew. Chem.; vol. 128; nb. 1; (2016); p. 296 - 299,4 View in Reaxys

21 %

With MnCl2∙4H2O, water, m-chloroperbenzoic acid, Ru(4,4′,4''-tri-t-butyl-2,2′;6,2″-terpyridine)Cl3 in acetonitrile, Time= 2h, T= 0 °C , chemoselective reaction Kamijo, Shin; Amaoka, Yuuki; Inoue, Masayuki; Synthesis; nb. 14; (2010); p. 2475 - 2489; Art.No: E27210SS View in Reaxys With methyl(trifluoromethyl)dioxirane in dichloromethane, T= 0 °C , also with dimethyldioxirane in CH2Cl2/acetone, Rate constant Mello, Rossella; Fiorentino, Michele; Fusco, Caterina; Curci, Ruggero; Journal of the American Chemical Society; vol. 111; nb. 17; (1989); p. 6749 - 6757 View in Reaxys With trans-lt;RuL1O2gt;2+ (L1 = 6,7,14,15,16,17,18,19-octahydro-14,18-dimethyl-13H-dibenzolt;e,ngt;lt; 1,4,8,12gt;dioxadiazacyclopentadecine, water in acetonitrile, T= 24.9 °C , ΔH(excit.), ΔS(excit.); other conditions: other reagents, other temperatures, Kinetics, Thermodynamic data, Mechanism Che, Chi-Ming; Tang, Wai-Tong; Wong, Kwok-Yin; Li, Chi-Keung; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 12; (1991); p. 3277 - 3280 View in Reaxys With lithium aluminium tetrahydride, 2,2'-azobis(isobutyronitrile), oxygen, relative chain propagation rates, Kinetics Pritzkow, Wilhelm; Thomas, Gerda; Willecke, Lothar; Journal fuer Praktische Chemie (Leipzig); vol. 327; nb. 6; (1985); p. 945 - 952 View in Reaxys With cis-lt;Ru(VI)(N,N,N',N'-tetramethyl-3,6-diazaoctane-1,8-diamine)O2gt;(2+) in acetonitrile, T= 24.9 °C , other temperatures; ΔH(excit.); ΔS(excit.), Kinetics, Thermodynamic data Cheng, Wing-Chi; Yu, Wing-Yiu; Li, Chi-Kueng; Che, Chi-Ming; Journal of Organic Chemistry; vol. 60; nb. 21; (1995); p. 6840 - 6846 View in Reaxys With methyl(trifluoromethyl)dioxirane in acetone, T= 0 °C , Rate constant

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Fusco, Caterina; Florentino, Michele; Dinoi, Anna; Curci, Ruggero; Krause, Ralph A.; Kuck, Dietmar; Journal of Organic Chemistry; vol. 61; nb. 24; (1996); p. 8681 - 8684 View in Reaxys 100 % Chromat.

With [FeF(octaethylporphyrinate)] hydrate, 18-crown-6 nitrite in acetic acid, T= 50 °C , Rate constant O'Shea, Stephen K.; Wang, Wen; Wade, Ruth S.; Castro, Charles E.; Journal of Organic Chemistry; vol. 61; nb. 18; (1996); p. 6388 - 6395 View in Reaxys With cobalt naphthenate, oxygen Tsutsumi et al.; ; vol. 35; (1956); p. 518,525; ; (1957); p. 4302 View in Reaxys With air, aluminium Patent; Universal Oil Prod. Co.; US2614130; (1949) View in Reaxys With air, lead dioxide Patent; Allied Chem. and Dye Corp.; US2743300; (1951) View in Reaxys With chromium(VI) oxide, acetic acid Boedtker; Bulletin de la Societe Chimique de France; vol. <3> 25; (1901); p. 851 View in Reaxys With potassium permanganate, acetic acid Boedtker; Bulletin de la Societe Chimique de France; vol. <3> 25; (1901); p. 851 View in Reaxys With calcium carbonate, copper(II) oxide, T= 100 - 110 °C , Einleiten von Luft Patent; I.G. Farbenind.; US1813606; (1927) View in Reaxys Patent; I.G. Farbenind.; DE522255; (1926); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 766 View in Reaxys

17 % Chromat.

With hexadecyldimethylbenzylammonium chloride, 4-tert-butylpyridine, TDCPP-Mn in dichloromethane, Time= 0.166667h, T= 20 °C Querci, Cecilia; Ricci, Marco; Tetrahedron Letters; vol. 31; nb. 12; (1990); p. 1779 - 1782 View in Reaxys With oxygen, Time= 24h, Ambient temperature, Irradiation, Yield given Pasternak, Mordechai; Morduchowitz, Abraham; Tetrahedron Letters; vol. 24; nb. 40; (1983); p. 4275 - 4278 View in Reaxys With trans-lt;Ru(VI)(dmpipy)2O2gt;lt;ClO4gt;2 in acetonitrile, Time= 4h, Ambient temperature Che, Chi-Ming; Leung, Wai-Ho; Li, Chi-Keung; Poon, Chung-Kwong; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 3; (1991); p. 379 - 384 View in Reaxys

13.4 % Chromat.

With dimethyldioxiran in acetone, Time= 72h, Ambient temperature Kuck, Dietmar; Schuster, Andreas; Zeitschrift fuer Naturforschung, B: Chemical Sciences; vol. 46; nb. 9; (1991); p. 1223 - 1226 View in Reaxys With bromine, B-iPr-9-BBN in dichloromethane, Time= 1h, T= 0 °C Brown, Herbert C.; Lane, Clinton F.; de Lue, Norman R.; Tetrahedron; vol. 44; nb. 10; (1988); p. 2773 - 2784

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View in Reaxys With methyl(trifluoromethyl)dioxirane in dichloromethane, Time= 0.166667h, T= 0 °C , Yield given Mello, Rossella; Fiorentino, Michele; Fusco, Caterina; Curci, Ruggero; Journal of the American Chemical Society; vol. 111; nb. 17; (1989); p. 6749 - 6757 View in Reaxys With lithium aluminium tetrahydride, oxygen, dibenzoyl peroxide, 1.) 125 deg C, Multistep reaction Heinze, Antje; Lauterbach, Gerlinde; Pritzkow, Wilhelm; Schmidt-Renner, Wolfgang; Voerckel, Volkmar; Zewegsuren, Nansadyn; Journal fuer Praktische Chemie (Leipzig); vol. 329; nb. 3; (1987); p. 439 - 446 View in Reaxys With Mo(VI)(O)2(NCS)2(4,4'-tBu2-bipy), Time= 6h, Ambient temperature, Irradiation, Yield given Arzoumanian, Henri; Agrifoglio, Giuseppe; Krentzien, Heinz; Capparelli, Mario; Journal of the Chemical Society, Chemical Communications; nb. 6; (1995); p. 655 - 656 View in Reaxys 26 % Chromat.

With potassium permanganate, boron trifluoride acetonitrile complex in acetonitrile, T= 24.85 °C , Kinetics Lam, William W. Y.; Yiu, Shek-Man; Lee, Joyce M. N.; Yau, Sammi K. Y.; Kwong, Hoi-Ki; Lau, Tai-Chu; Liu, Dan; Lin, Zhenyang; Journal of the American Chemical Society; vol. 128; nb. 9; (2006); p. 2851 - 2858 View in Reaxys 12 :EXAMPLE 12; The same procedure is effected as in Example 11 without N-hydroxyphthalimide ; a conversion of 4percent of cumene in cumyl alcohol is obtained. With oxygen, dimethyldioxiran in acetone, Time= 12h, T= 20 °C , Conversion of starting material Patent; POLIMERI EUROPA S.P.A.; POLITECNICO DI MILANO; WO2008/37435; (2008); (A1) English View in Reaxys

12 %Chromat.

With PEG-1000, carbon dioxide, oxygen, anhydrous cobalt diacetate, Time= 12h, T= 100 °C , p= 75007.5Torr , Autoclave, Neat (no solvent) Wang, Jin-Quan; He, Liang-Nian; New Journal of Chemistry; vol. 33; nb. 8; (2009); p. 1637 - 1640 View in Reaxys With m-chloroperbenzoic acid in acetonitrile, Time= 1h, T= 23 °C , Inert atmosphere Goldsmith, Christian R.; Coates, Cristina M.; Hagan, Kenton; Mitchell, Casey A.; Journal of Molecular Catalysis A: Chemical; vol. 335; nb. 1-2; (2011); p. 24 - 30 View in Reaxys With di(hydroxo)germanium (5,10,15,20-tetraphenylporphyrin) / silica gel composite in water, Irradiation, Inert atmosphere Shiragami, Tsutomu; Shiraki, Ryuichi; Makise, Ryuichi; Matsumoto, Jin; Yasuda, Masahide; Chemistry Letters; vol. 39; nb. 8; (2010); p. 874 - 875 View in Reaxys With C20H28N6Ni(2+)*2C24H20B, m-chloroperbenzoic acid in dichloromethane, acetonitrile, Time= 1h, T= 20 °C , Inert atmosphere Balamurugan, Mani; Mayilmurugan, Ramasamy; Suresh, Eringathodi; Palaniandavar, Mallayan; Dalton Transactions; vol. 40; nb. 37; (2011); p. 9413 - 9424 View in Reaxys

32 %Chromat.

With Oxonetrade;, 1,1,1-trifluoro-2-propanone, sodium hydrogencarbonate, cycloheptaamylose in water, Time= 8h, T= 20 °C Fung, Yat-Sing; Yan, Siu-Cheong; Wong, Man-Kin; Organic and Biomolecular Chemistry; vol. 10; nb. 15; (2012); p. 3122 - 3130 View in Reaxys

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36 %Chromat.

With tert -butyl hydrogen peroxide, 4C48H36N6*4Cu(1+)*4NO3 (1-) in water, acetonitrile, Time= 24h, T= 60 °C He, Qi-Ting; Li, Xiang-Ping; Chen, Lian-Fen; Zhang, Li; Wang, Wei; Su, Cheng-Yong; ACS Catalysis; vol. 3; nb. 1; (2013); p. 1 - 9 View in Reaxys

45.6 2.3. Reactivity studies %Chromat. General procedure: The oxidation of alkanes was carried out at room temperature under research grade nitrogen atmosphere. In a typical reaction, Ni(II) complex (0.35 x 10–3 mmol dm-3) was added to a mixture of alkanes (2.45 mol dm-3) and oxidant m-CPBA (0.35 mol dm-3) in CH2Cl2:CH3CN mixture (3:1 v/v). After 4 h the reaction mixture was quenched with triphenylphosphine, the reaction mixture was filtered over a silica column and then eluted with diethylether. An internal standard (bromobenzene) was added at this point and the solution was subjected to GC analysis. The mixture of organic products were identified by Agilent GC–MS and quantitatively analyzed by HP 6890 series GC equipped with HP-5 capillary column (30 m x 0.32 mm x 2.5 μm) using a calibration curve obtained with authentic compounds. All of the products were quantified using GC (FID) with the following temperature program: inject or temperature 130 °C; initial temperature 60 °C, heating rate 10 °C min-1 to 130 °C, increasing the temperature to 160 °C at a rate of 2 °C min-1, and then increasing the temperature to 260 °C at a rate of 5 C min-1; FID temperature 280 °C. GC–MS analysis was performed under conditions identical to those used for GC analysis. The averages of three measurements are reported. With [Ni(picolinic acid)(N,N',N''-pentamethyldiethylenetriamine)(CH3CN)](BPh4), m-chloroperbenzoic acid in dichloromethane, acetonitrile, Time= 4h, T= 20 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst Sankaralingam, Muniyandi; Vadivelu, Prabha; Suresh, Eringathodi; Palaniandavar, Mallayan; Inorganica Chimica Acta; vol. 407; (2013); p. 98 - 107 View in Reaxys 21.4 2.4. Catalytic oxidations %Chromat. General procedure: In a typical reaction, the oxidant m-CPBA (0.8 mol dm-3) wasadded to a mixture of the diiron(III) complex (1 Χ 103 mmol dm-3)and the alkanes (3 mol dm-3) in a CH2Cl2:CH3CN mixture (4:1 v/v). After 30 min the reaction mixture was quenched with triphenylphosphine, the reaction mixture was filtered over a silica column and then eluted with diethylether. An internal standard (bromobenzene) was added at this point and the solution was subjected to GC analysis. The mixture of organic products was identified by GC-MS and quantitatively analyzed by HP 6890 series GC equipped with an HP-5 capillary column (30 m Χ 0.32 Χ mm 2.5 lm) using a calibration curve obtained with authentic compounds. All of the products were quantified using GC (FID) with the following temperature program: injector temperature 130 °C; initial temperature 60 °C, heating rate 10 °C min-1 to 130 °C, increasing the temperature to 160 °C at a rate of 2 °C min-1, and then increasing the temperature to 260 °C at a rate of 5 °C min-1; FID temperature 280 °C. GC-MS analysis was performed under conditions identical to those used for GC analysis. The averages of three measurements are reported. With [Fe2(O)(benzoate)2(bis(pyridin-2-ylmethyl)amine)2](ClO4)2, m-chloroperbenzoic acid in dichloromethane, acetonitrile, Time= 0.5h, T= 20 °C , Catalytic behavior, Reagent/catalyst Sankaralingam, Muniyandi; Palaniandavar, Mallayan; Polyhedron; vol. 67; (2014); p. 171 - 180 View in Reaxys With Iron (III) nitrate nonahydrate, tppGe(OH)2, oxygen, potassium hydroxide in methanol, water, Irradiation, Kinetics, Quantum yield, Catalytic behavior, Reagent/catalyst Shiragami, Tsutomu; Kuroki, Ayano; Matsumoto, Jin; Yasuda, Masahide; Journal of Porphyrins and Phthalocyanines; vol. 18; nb. 7; (2014); p. 529 - 534 View in Reaxys With hydrogen peroxide in acetonitrile, Time= 1.5h, T= 40 °C , Catalytic behavior Feng, Yan; Moschetta, Eric G.; Jones, Christopher W.; Chemistry - An Asian Journal; vol. 9; nb. 11; (2014); p. 3142 - 3152 View in Reaxys With Iron (III) nitrate nonahydrate, tppGe(OH)2 in methanol, T= 20 °C , Irradiation, Inert atmosphere, Kinetics, Mechanism, Quantum yield Shiragami, Tsutomu; Kuroki, Ayano; Matsumoto, Jin; Yasuda, Masahide; Journal of Porphyrins and Phthalocyanines; vol. 18; nb. 7; (2014); p. 529 - 534

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View in Reaxys With bromotrichloromethane, carbon tetrabromide, C29H33FeN5O3 (2+)*2CF3O3S(1-) in acetonitrile, Time= 24h Rana, Sujoy; Dey, Aniruddha; Maiti, Debabrata; Chemical Communications; vol. 51; nb. 77; (2015); p. 14469 14472 View in Reaxys

O O

Rx-ID: 2071796 View in Reaxys 7/487 Yield 30 %, 23 %, 33 %, 26 %

Conditions & References With trimethylhexadecylammonium chloride, copper dichloride in water, T= 20 - 25 °C , Irradiation, Further byproducts given Turro, Nicholas J.; Mattay, Jochen; Journal of the American Chemical Society; vol. 103; nb. 14; (1981); p. 4200 4204 View in Reaxys

30 %, 26 %, 33 %, 23 %

With trimethylhexadecylammonium chloride, copper dichloride in water, T= 20 - 25 °C , Irradiation, Further byproducts given Turro, Nicholas J.; Mattay, Jochen; Journal of the American Chemical Society; vol. 103; nb. 14; (1981); p. 4200 4204 View in Reaxys With copper dichloride in water, Irradiation, Further byproducts given. Title compound not separated from byproducts Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802 View in Reaxys With copper dichloride in water, Irradiation, Further byproducts given. Title compound not separated from byproducts Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802 View in Reaxys With copper dichloride in water, Irradiation, Further byproducts given. Title compound not separated from byproducts Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802 View in Reaxys

O Br

Rx-ID: 3522991 View in Reaxys 8/487 Yield 95 %

Conditions & References With lithium in diethyl ether, Time= 0.5h, ultrasonic agitation Luche, Jean-Louis; Damiano, Jean-Claude; Journal of the American Chemical Society; vol. 102; nb. 27; (1980); p. 7926 - 7927 View in Reaxys

61 %

With magnesium in diethyl ether, Time= 3h, Heating Bors, Daniel A.; Kaufman, Michael J.; Streitwieser, Andrew Jr.; Journal of the American Chemical Society; vol. 107; nb. 24; (1985); p. 6975 - 6982 View in Reaxys

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Rx-ID: 9240942 View in Reaxys 9/487 Yield

Conditions & References With 2,2'-azo-bisisobutyronitrile, oxygen, copper, T= 60 °C , Product distribution, Kinetics, Further Variations: Reagents Fedushchak; Il'ln; Russian Journal of Applied Chemistry; vol. 75; nb. 3; (2002); p. 345 - 350 View in Reaxys With oxygen in dichloromethane, Time= 4h, T= 20 °C , p= 760.051Torr , Irradiation Carraro, Mauro; Gardan, Martino; Scorrano, Gianfranco; Drioli, Enrico; Fontananova, Enrica; Bonchio, Marcella; Chemical Communications; nb. 43; (2006); p. 4533 - 4535 View in Reaxys

9.1 With oxygen, benzoic acid, Time= 3h, T= 140 °C , Neat (no solvent) %ChroBeier, Matthias J.; Schimmoeller, Bjoern; Hansen, Thomas W.; Andersen, Jens E.T.; Pratsinis, Sotiris E.; mat., 9.5 %Chromat. Grunwaldt, Jan-Dierk; Journal of Molecular Catalysis A: Chemical; vol. 331; nb. 1-2; (2010); p. 40 - 49 View in Reaxys With 2-hydroxy-1,3-isoindolinedione, oxygen, acetaldehyde in acetonitrile, Time= 6h, T= 45 °C , p= 760.051Torr Melone, Lucio; Gambarotti, Cristian; Prosperini, Simona; Pastori, Nadia; Recupero, Francesco; Punta, Carlo; Advanced Synthesis and Catalysis; vol. 353; nb. 1; (2011); p. 147 - 154 View in Reaxys With 2-hydroxy-1,3-isoindolinedione, oxygen, acetaldehyde in carbonic acid dimethyl ester, Time= 6h, T= 25 °C , p= 760.051Torr Melone, Lucio; Gambarotti, Cristian; Prosperini, Simona; Pastori, Nadia; Recupero, Francesco; Punta, Carlo; Advanced Synthesis and Catalysis; vol. 353; nb. 1; (2011); p. 147 - 154 View in Reaxys 420 mmol, 24 mmol

89 mmol, 549 mmol

With tert.-butylhydroperoxide, tert-butyl benzene, meso-1,2-diphenylethylene Crites, Charles-Oneil L.; Hallet-Tapley, Geniece L.; Gonzalez-Bejar, Maria; Netto-Ferreira; Scaiano, Juan C.; Chemical Communications; vol. 50; nb. 18; (2014); p. 2289 - 2291 View in Reaxys With oxygen, 4-hexyloxycarbonyl N-hydroxyphthalimide in acetonitrile, T= 60 °C , p= 760.051Torr , Solvent, Reagent/catalyst Kasperczyk, Kornela; Orlinska, Beata; Zawadiak, Jan; Central European Journal of Chemistry; vol. 12; nb. 11; (2014); p. 1176 - 1182 View in Reaxys The liquid oxidation reactions were carried out in a three-necked flask (20 mL), supplied with a magnetic stirrer, refluxcondenser and the oil bath. Cumene (10 mL) and catalyst were put into the flask, sonicated for 5 min, and then heated to preconcertedtemperature followed by the bubbling of oxygen at a constant flowrate. The main product of cumene oxidation is CHP, the by-productsare acetophenone (AP) and 2-benzyl-2-propanol (BP), as shownin Scheme 1. The CHP concentration was determined accordingto the iodometric method [24]. After the reduction of generatedCHP to BP via triphenylphosphine reaction [25], the other prod-ucts in the liquid phase were detected by gas chromatography (anAgilent GC-6820) equipped with a 30 m × 0.25 mm × 0.25 m HP-5capillary column and a flame ionization detector (detector tem-perature 553 K, injector temperature 553 K, and oven temperature413 K) using toluene as external standard. Cumene conversion (X)and products selectivity (S) were calculated using the followingequations (I)–(IV).

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With graphite, oxygen, Time= 8h, T= 79.84 °C , p= 760.051Torr Liao, Shixia; Peng, Feng; Yu, Hao; Wang, Hongjuan; Applied Catalysis A: General; vol. 478; (2014); p. 1 - 8 View in Reaxys

Rx-ID: 30793660 View in Reaxys 10/487 Yield

Conditions & References Reaction of 2-methyl-2-phenylpropanal (4)in water: A mixture of 4 (1.05 g, 0.007 mol) in 10 mL of water was stirred at room temperature and under air. After 31 days the organics were extracted with diethyl ether, dried with MgSO4, and the solvent was removed under vacuum to yield a yellow oil (crude). The obtained crude was properly characterized (NMR) and identified as being a mixture of 2-phenyl-2-propanol 6 and cumene hydroperoxide 7 (0.42 g, 39-44percent) by comparison with authentic samples. With water, oxygen, Time= 744h, T= 20 °C Rodrigues, Catarina A.B.; De Matos, Marta Norton; Guerreiro, Bruno M.H.; Goncalves, Ana M.L.; Romao, Carlos C.; Afonso, Carlos A.M.; Tetrahedron Letters; vol. 52; nb. 22; (2011); p. 2803 - 2807 View in Reaxys With Rh2(OAc)4, 3β-acetoxycholest-5-ene, oxygen in 1,2-dichloro-ethane Shabashov, Dmitry; Doyle, Michael P.; Tetrahedron; vol. 69; nb. 47; (2013); p. 10009 - 10013 View in Reaxys

Rx-ID: 3923386 View in Reaxys 11/487 Yield 94 %

Conditions & References With oxygen, TEAB, Co(TPP) in ethylene glycol dimethyl ether, isopropyl alcohol, Time= 48h, Ambient temperature Okamoto, Tadashi; Oka, Shinzaburo; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1589 - 1594 View in Reaxys

56 %

With cis-lt;RuIVLO2gt;lt;ClO4gt;2 (L = N,N,N',N',3,6-hexamethyl-3,6-diazaoctane-1,8-diamine) in acetonitrile, T= 25 °C Li, Chi-Keung; Che, Chi-Ming; Tong, Wai-Fong; Tang, Wai-Tong; Wong, Kwok-Yin; Lai, Ting-Fong; Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999); nb. 13; (1992); p. 2109 - 2116 View in Reaxys

28 % Chromat.

With sodium tetrahydroborate, oxygen, (pyridine)Co(dimethylglyoxime)2Cl in dimethyl sulfoxide, Time= 60h Okamoto, Tadashi; Oka, Shinzaburo; Tetrahedron Letters; vol. 22; nb. 23; (1981); p. 2191 - 2194 View in Reaxys With triethylsilane, lt;5,10,15,20-tetrakis(2,6-dichlorophenyl)porphinatogt;cobalt(II), oxygen, phosphorous acid trimethyl ester, 1.) 2-propanol, dichloromethane, 28 deg C, 1 atm, 30 min, 2.) 2-propanol, dichloromethane, RT, 2 h, Yield given. Multistep reaction Matsusita, Yoh-ichi; Sugamoto, Kazuhiro; Matsui, Takanao; Chemistry Letters; nb. 6; (1993); p. 925 - 928 View in Reaxys With sulfuric acid in methanol, T= 25 °C , Kinetics, Further Variations: reagent concentrations Pytela, Oldrich; Trlida, Bronislav; Collection of Czechoslovak Chemical Communications; vol. 72; nb. 8; (2007); p. 1025 - 1036 View in Reaxys

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paraformaldehyde

Rx-ID: 5690973 View in Reaxys 12/487 Yield

Conditions & References

76 %, 19.3 %, 5.8 %, 11 %

With chlorhexidine diphosphanilate in acetonitrile, Time= 48h, T= 100 °C , Further byproducts given

11.0 %, 76.0 %, 5.8 %, 19.9 %

With chlorhexidine diphosphanilate in acetonitrile, Time= 48h, T= 100 °C , Further byproducts given

11.0 %, 19.3 %, 5.8 %, 76 %

With chlorhexidine diphosphanilate in acetonitrile, Time= 48h, T= 100 °C , Further byproducts given

Humphreys, Robert W. R.; Journal of Organic Chemistry; vol. 48; nb. 9; (1983); p. 1483 - 1487 View in Reaxys

(v2)

Rx-ID: 8519794 View in Reaxys 13/487 Yield

Conditions & References

81 %

Stage 1: With VCl4 in tetrahydrofuran, hexane, Time= 1h, T= -78 °C , complexation Stage 2: in tetrahydrofuran, hexane, Time= 10h, T= 20 °C , Methylation Kataoka, Yasutaka; Makihira, Isamu; Utsunomiya, Masaru; Tani, Kazuhide; Journal of Organic Chemistry; vol. 62; nb. 24; (1997); p. 8540 - 8543 View in Reaxys

I O

Rx-ID: 10073626 View in Reaxys 14/487 Yield

Conditions & References

96 %

With strontium in tetrahydrofuran, Time= 0.5h, T= 20 °C , Barbier reaction Miyoshi, Norikazu; Matsuo, Tsuyoshi; Wada, Makoto; European Journal of Organic Chemistry; nb. 20; (2005); p. 4253 - 4255 View in Reaxys O O

I HO

Rx-ID: 10073679 View in Reaxys 15/487 Yield 96 %

Conditions & References With strontium in tetrahydrofuran, Time= 0.5h, T= 20 °C , Barbier reaction Miyoshi, Norikazu; Matsuo, Tsuyoshi; Wada, Makoto; European Journal of Organic Chemistry; nb. 20; (2005); p. 4253 - 4255 View in Reaxys

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Rx-ID: 10073686 View in Reaxys 16/487 Yield 91 %

Mg Cl O

Rx-ID: 10318810 View in Reaxys 17/487 Yield 80 %

Conditions & References With 1-butyl-2-isopropyl-3-methylimidazolium triflimide in tetrahydrofuran, T= 20 °C Handy, Scott T.; Journal of Organic Chemistry; vol. 71; nb. 12; (2006); p. 4659 - 4662 View in Reaxys

O HO

Rx-ID: 23047564 View in Reaxys 18/487 Yield

Conditions & References 1 : EXAMPLE 1 EXAMPLE 1 A standard stock oxidation mixture was prepared containing an amount of sec-butyl benzene (SBB), and an amount of cumene effective to produce a weight ratio of SBB:cumene of 3.4:1.The stock oxidation mixture also contained 1percent cumene hydroperoxide as an initiator.In all experiments described below, 300 grams of the oxidation mixture was exposed to oxidation conditions comprising a temperature of 130° C., an oxidizing agent comprising 500 cc/ min. 7percent O2 in N2, and a steady pressure of 40 psig.All experiments were carried out in a 500 cc Buchi Type II reactor, with a stirring rate of 1300 rpm. The foregoing stock oxidation mixture was used in a control oxidation to provide a comparative example to assess the effect of ammonia on the reaction.Neither ammonia nor water was added to the control experiment.After 8 hours, the mixture contained 340 wppm formic acid, 752 wppm acetic acid, and 515 wppm phenol. In a first comparative experiment, during the oxidation, gaseous NH3 was bubbled through the oxidation mixture at a molar ratio of 1.28 to 1 based on the expected acid production, resulting in an ammonia feed rate of 0.379 cc/min at STP. No water was added in this experiment. [0031] In a second comparative experiment, 1.25 wt. percent water was charged to the standard oxidation mixture, and during the oxidation, gaseous ammonia was bubbled through the oxidation mixture at a molar ratio of NH3 to expected acid production of 1.28 to 1, resulting in a feed rate of the aqueous ammonia of 0.375 cc/min. at STP. [0032] Measurements of cumene hydroperoxide (CHP), s-butylbenzene hydroperoxide (sBBHP), AP, DMBA, and EMBA were taken every hour, after the reaction temperature reached designed temperature and NH3 feed started. All results listed below are in percent wt: With ammonia, oxygen, Time= 1 - 8h, T= 130 °C , p= 2068.65Torr Patent; Yang, Jiemin; Black, Jesse Raymond; US2004/162448; (2004); (A1) English View in Reaxys 3 : EXAMPLE 3 The same standard oxidation experiment as mentioned in Example 1 and Example 2 was used as a control oxidation to provide a comparative example to assess the effect of sodium carbonate on the reaction. Neither sodium carbonate nor water was added to the control mixture. After 8 hours, the mixture contained 340 wppm formic acid, 752 wppm acetic acid and 515 wppm phenol. [0042] In a comparative experiment, 0.95 g of water along with 0.3 grams

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of Na2CO3 was added into 300 grams of standard oxidation feed. This resulted in a molar ratio of Na2CO3 to expected acids of 0.9:1 in the oxidation mixture. Compared to the control experiment, total hydroperoxide yield at the end of the 8 hour run increased by 17.1percent. Interpolating the experimental results to 25 wt. percent total hydroperoxides, the Na2CO3 charged oxidation mixture achieved an AP reduction of 28.7percent and a DMBA+EMBA reduction of 33percent. With water, oxygen, sodium carbonate, Time= 1 - 8h, T= 130 °C , p= 2068.65Torr Patent; Yang, Jiemin; Black, Jesse Raymond; US2004/162448; (2004); (A1) English View in Reaxys 1 : EXAMPLE 1 EXAMPLE 1 A standard stock oxidation mixture was prepared containing an amount of sec-butyl benzene (SBB), and an amount of cumene effective to produce a weight ratio of SBB:cumene of 3.4:1.The stock oxidation mixture also contained 1percent cumene hydroperoxide as an initiator.In all experiments described below, 300 grams of the oxidation mixture was exposed to oxidation conditions comprising a temperature of 130° C., an oxidizing agent comprising 500 cc/ min. 7percent O2 in N2, and a steady pressure of 40 psig.All experiments were carried out in a 500 cc Buchi Type II reactor, with a stirring rate of 1300 rpm. The foregoing stock oxidation mixture was used in a control oxidation to provide a comparative example to assess the effect of ammonia on the reaction.Neither ammonia nor water was added to the control experiment.After 8 hours, the mixture contained 340 wppm formic acid, 752 wppm acetic acid, and 515 wppm phenol. In a first comparative experiment, during the oxidation, gaseous NH3 was bubbled through the oxidation mixture at a molar ratio of 1.28 to 1 based on the expected acid production, resulting in an ammonia feed rate of 0.379 cc/min at STP. No water was added in this experiment. [0031] In a second comparative experiment, 1.25 wt. percent water was charged to the standard oxidation mixture, and during the oxidation, gaseous ammonia was bubbled through the oxidation mixture at a molar ratio of NH3 to expected acid production of 1.28 to 1, resulting in a feed rate of the aqueous ammonia of 0.375 cc/min. at STP. [0032] Measurements of cumene hydroperoxide (CHP), s-butylbenzene hydroperoxide (sBBHP), AP, DMBA, and EMBA were taken every hour, after the reaction temperature reached designed temperature and NH3 feed started. All results listed below are in percent wt: With ammonia, water, oxygen, Time= 1 - 8h, T= 130 °C , p= 2068.65Torr Patent; Yang, Jiemin; Black, Jesse Raymond; US2004/162448; (2004); (A1) English View in Reaxys

Rx-ID: 1709976 View in Reaxys 19/487 Yield 78 %, 17 %

Conditions & References With KBrO3, cerium (IV) oxide in 1,4-dioxane, water, acetic acid, Time= 2h, T= 95 °C Akhlaghinia, Batool; Ebrahimabadi, Hossein; Goharshadi, Elaheh K.; Samiee, Sara; Rezazadeh, Soodabeh; Journal of Molecular Catalysis A: Chemical; vol. 357; (2012); p. 67 - 72 View in Reaxys

30.4 %, 2.9 %

With oxygen, Mn(II)-complex, Time= 65h, T= 30 °C , different temperatures, times, catalysts, Product distribution Sawodny, Wolfgang; Gruenes. Reinhard; Reitzle, Helmut; Angewandte Chemie; vol. 94; nb. 10; (1982); p. 803 View in Reaxys

6.9 %, 5.4 %

With air, zinc, iron(II) chloride in pyridine, acetic acid, Time= 16h, Ambient temperature Barton; Halley; Ozbalik; Mehl; Tetrahedron Letters; vol. 30; nb. 48; (1989); p. 6615 - 6618 View in Reaxys

5.4 %, 6.9 %

With air, zinc, iron(II) chloride in pyridine, acetic acid, Time= 16h, Ambient temperature, Product distribution, Mechanism Barton; Halley; Ozbalik; Mehl; Tetrahedron Letters; vol. 30; nb. 48; (1989); p. 6615 - 6618 View in Reaxys

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5.4 %, 6.9 %

With air, zinc, iron(II) chloride in pyridine, acetic acid, Time= 16h, Ambient temperature Barton; Halley; Ozbalik; Mehl; Tetrahedron Letters; vol. 30; nb. 48; (1989); p. 6615 - 6618 View in Reaxys

20 % Chromat., 5 % Chromat.

With NBun 4MnO4, acetic acid, Time= 10h, T= 35 - 40 °C Leddy, Bernard P.; McKervey, M.Antony; McSweeney, Peter; Tetrahedron Letters; vol. 21; (1980); p. 2261 - 2264 View in Reaxys With hydrogen peroxide, ruthenium trichloride, N,N-didecyl-N,N-dimethylammonium bromide, Time= 4.5h, T= 80 °C , Yield given. Yields of byproduct given Barak, Gabriela; Sasson, Yoel; Journal of the Chemical Society, Chemical Communications; nb. 10; (1988); p. 637 - 638 View in Reaxys

8 % Chromat., 64 % Chromat.

46 % Chromat., 29 % Chromat.

With oxygen, N -hydroxyphthalimide in benzonitrile, Time= 20h, T= 100 °C , p= 760Torr Ishii, Yasutaka; Nakayama, Kouichi; Takeno, Mitsuhiro; Sakaguchi, Satoshi; Iwahama, Takahiro; Nishiyama, Yutaka; Journal of Organic Chemistry; vol. 60; nb. 13; (1995); p. 3934 - 3935 View in Reaxys With N -hydroxyphthalimide, oxygen, acetaldehyde in acetonitrile, Ambient temperature Einhorn, Cathy; Einhorn, Jacques; Marcadal, Celine; Pierre, Jean-Louis; Chemical Communications; nb. 5; (1997); p. 447 - 448 View in Reaxys With air, trans-lt;OsO2(CN)2(4,7-diphenyl-1,10-phenanthroline)gt; in dichloromethane, Time= 12h, Irradiation, Yield given. Yields of byproduct given. Title compound not separated from byproducts Cheng, Jack Y. K.; Cheung, Kung-Kai; Che, Chi-Ming; Lau, Tai-Chu; Chemical Communications; nb. 15; (1997); p. 1443 - 1444 View in Reaxys With zeolite HY20, oxygen, Titanium(IV) oxide in acetonitrile, Time= 72h, Irradiation, also with α-methylstyrene; photooxidation without zeolite too; var. reaction times, Product distribution Beaune, Olivia; Finiels, Annie; Geneste, Patrick; Graffin, Patrick; Olive, Jean-Louis; Saaedan, Ahmed; Journal of the Chemical Society, Chemical Communications; nb. 22; (1992); p. 1649 - 1650 View in Reaxys With hydrogen peroxide, ruthenium trichloride, dimethyl-didodecyl-ammonium bromide, Time= 4.5h, T= 80 °C , further alkyl aromatic compounds, further transition metal salts, phase-transfer catalysts Barak, Gabriela; Sasson, Yoel; Journal of the Chemical Society, Chemical Communications; nb. 10; (1988); p. 637 - 638 View in Reaxys With oct-1-ene, oxygen, PCoW-Keggin type polyoxotungstate in acetonitrile, Time= 24h, T= 80 °C , p= 760Torr , var. of catalyst, Product distribution Neumann, Ronny; Dahan, Mazal; Journal of the Chemical Society, Chemical Communications; nb. 2; (1995); p. 171 - 172 View in Reaxys With chelate Cu complex on silica, oxygen in various solvent(s), T= 90 °C , also Ni chelate complexes, Product distribution Mingalev; Sadikova; Kuznetsov; Filippova; Petroleum Chemistry; vol. 37; nb. 3; (1997); p. 240 - 244 View in Reaxys

5 % Chromat., 20 % Chromat.

With NBun 4MnO4, acetic acid, Time= 10h, T= 35 - 40 °C Leddy, Bernard P.; McKervey, M.Antony; McSweeney, Peter; Tetrahedron Letters; vol. 21; (1980); p. 2261 - 2264

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View in Reaxys 64 % Chromat., 8 % Chromat. 29 % Chromat., 46 % Chromat.

61 % Chromat., 29 % Chromat.

With tert -butyl hydrogen peroxide, cis-[RuII(6,6'-Cl2bpy)2(OH)2](CF3SO3)2 in acetone, Time= 0.4h, T= 20 °C , Oxidation Che; Cheng; Chan; Lau; Mak; Journal of Organic Chemistry; vol. 65; nb. 23; (2000); p. 7996 - 8000 View in Reaxys With iodosylbenzene, {[Fe(IV)(O)(N4Py)](ClO4)}+ in acetonitrile, T= 25 °C , Product distribution, Kinetics, Further Variations: Reagents Kaizer, Jozsef; Klinker, Eric J.; Oh, Na Young; Rohde, Jan-Uwe; Song, Woon Ju; Stubna, Audria; Kim, Jinheung; Muenck, Eckard; Nam, Wonwoo; Que Jr., Lawrence; Journal of the American Chemical Society; vol. 126; nb. 2; (2004); p. 472 - 473 View in Reaxys

80 % Chromat., 9 % Chromat.

With 2,6-dichloropyridine-N-oxide in benzene, T= 20 °C

13.5 % Chromat., 39.7 % Chromat.

With tert -butyl hydrogen peroxide, air, [Co(bdpm)(OBz)]ClO4 in acetonitrile, Time= 0.75h, T= 20 °C

Zhang, Rui; Yu, Wing-Yiu; Che, Chi-Ming; Tetrahedron Asymmetry; vol. 16; nb. 21; (2005); p. 3520 - 3526 View in Reaxys

Zhang; Liu; Peng; Du; Polish Journal of Chemistry; vol. 79; nb. 4; (2005); p. 655 - 661 View in Reaxys Stage 1: With triethylsilane, [Bu4N4]W10O32, oxygen in acetonitrile, Time= 2.5h, T= 5 - 10 °C , Irradiation Stage 2: With triphenylphosphine, Further stages. Lykakis, Ioannis N.; Orfanopoulos, Michael; Tetrahedron Letters; vol. 45; nb. 41; (2004); p. 7645 - 7649 View in Reaxys With air, cyclohexene, carbon, Time= 24h, Heating Sereda, Grigoriy; Rajpara, Vikul; Tetrahedron Letters; vol. 48; nb. 19; (2007); p. 3417 - 3421 View in Reaxys With oxygen in water, acetonitrile, T= 5 - 10 °C , p= 759.826Torr , Irradiation, chemoselective reaction Ni, Lingli; Ni, Ji; Lv, Yuan; Yang, Ping; Cao, Yong; Chemical Communications; nb. 16; (2009); p. 2171 - 2173 View in Reaxys With copper acetylacetonate, N -hydroxyphthalimide, oxygen, 1,1'-azobis(1-cyanocyclohexanenitrile) in benzonitrile, Time= 3h, T= 90 °C Orlinska, Beata; Tetrahedron Letters; vol. 51; nb. 31; (2010); p. 4100 - 4102 View in Reaxys Reaction Steps: 2

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1: hydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: hydrogen peroxide / water; acetonitrile / 24 h / 80 °C With hydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 2 1: hydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: hydrogen peroxide / water; acetonitrile / 24 h / 80 °C With hydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 2 1: hydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: hydrogen peroxide / water; acetonitrile / 24 h / 80 °C With hydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys Reaction Steps: 2 1: hydrogen peroxide / water; acetonitrile / 24 h / 80 °C 2: hydrogen peroxide / water; acetonitrile / 24 h / 80 °C With hydrogen peroxide in water, acetonitrile Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys 34 With C30H29N7ORu(2+)*2F6P(1-) in acetonitrile-d3, T= 20 °C , Inert atmosphere, Irradiation %Spectr., 6 %Spectr. Kojima, Takahiko; Nakayama, Kazuya; Sakaguchi, Miyuki; Ogura, Takashi; Ohkubo, Kei; Fukuzumi, Shunichi; Journal of the American Chemical Society; vol. 133; nb. 44; (2011); p. 17901 - 17911 View in Reaxys With [((tris(2-pyridylmethyl)amine))Fe(II)(acetonitrile)2](ClO4)2, oxygen in butanone, Time= 24h, T= 74.84 °C , p= 760.051Torr , Inert atmosphere, Molecular sieve Furukawa, Shinya; Hitomi, Yutaka; Shishido, Tetsuya; Tanaka, Tsunehiro; Inorganica Chimica Acta; vol. 378; nb. 1; (2011); p. 19 - 23 View in Reaxys With C17H19FeN5O5 (1-)*2C8H20N(1+), oxygen in acetonitrile, T= 25 °C , Kinetics Ghosh, Munmun; Singh, Kundan K.; Panda, Chakadola; Weitz, Andrew; Hendrich, Michael P.; Collins, Terrence J.; Dhar, Basab B.; Sen Gupta, Sayam; Journal of the American Chemical Society; vol. 136; nb. 27; (2014); p. 9524 - 9527 View in Reaxys With ammonium hydroxide, hydrogen peroxide in water, Time= 6.08333h, T= 79.84 °C , p= 760.051Torr Xia, Sheng; Yu, Tianhua; Liu, Huihui; Li, Guiying; Hu, Changwei; Catalysis Science and Technology; vol. 4; nb. 9; (2014); p. 3108 - 3119 View in Reaxys 82 %Spectr., 13 %Spectr.

With [Ce[Co(η5-C5H5){P(O)(OEt)2}3]2(H2O)2Cl] in neat (no solvent), T= 100 °C , Catalytic behavior Yi, Xiao-Yi; Wang, Guo-Cang; Ip, Ho-Fai; Wong, Wai-Yeung; Chen, Lizhuang; Sung, Herman H.-Y.; Williams, Ian D.; Leung, Wa-Hung; European Journal of Inorganic Chemistry; vol. 2014; nb. 35; (2014); p. 6097 - 6103

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View in Reaxys With Fe(V)(7,7,10,10,13,13-hexamethyl-5,7,8,12,13,15-hexahydro-5,8,12,15-tetraazabenzocyclotridecene-6,9,11,14-tetraone)O(1-) in acetonitrile, T= -30 °C , Kinetics, Temperature Kundu, Soumen; Van Thompson, Jasper Kirk; Shen, Longzhu Q.; Mills, Matthew R.; Bominaar, Emile L.; Ryabov, Alexander D.; Collins, Terrence J.; Chemistry - A European Journal; vol. 21; nb. 4; (2015); p. 1803 - 1810 View in Reaxys With C29H27FeN7O(2+)*2ClO4 (1-), T= 25 °C , Kinetics, Reagent/catalyst Mitra, Mainak; Nimir, Hassan; Demeshko, Serhiy; Bhat, Satish S.; Malinkin, Sergey O.; Haukka, Matti; LloretFillol, Julio; Lisensky, George C.; Meyer, Franc; Shteinman, Albert A.; Browne, Wesley R.; Hrovat, David A.; Richmond, Michael G.; Costas, Miquel; Nordlander, Ebbe; Inorganic Chemistry; vol. 54; nb. 15; (2015); p. 7152 7164 View in Reaxys With tert -butyl hydrogen peroxide in ethylbenzene, water, Time= 12h, T= 80 °C Yang, Shuliang; Peng, Li; Huang, Peipei; Wang, Xiaoshi; Sun, Yongbin; Cao, Changyan; Song, Weiguo; Angewandte Chemie - International Edition; vol. 55; nb. 12; (2016); p. 4016 - 4020; Angew. Chem.; vol. 128; nb. 12; (2016); p. 4084 - 4088,5 View in Reaxys

O HO

Rx-ID: 2037932 View in Reaxys 20/487 Yield

Conditions & References

95 %

With magnesium methanolate in methanol, Time= 6h, Ambient temperature Xu, Yao-Chang; Bizuneh, Amsalu; Walker, Clint; Journal of Organic Chemistry; vol. 61; nb. 26; (1996); p. 9086 9089 View in Reaxys

93 %

With magnesium in methanol, Time= 12h, Ambient temperature Xu, Yao-Chang; Lebeau, Elaine; Walker, Clint; Tetrahedron Letters; vol. 35; nb. 34; (1994); p. 6207 - 6210 View in Reaxys O

Rx-ID: 10073685 View in Reaxys 21/487 Yield 74 %

Rx-ID: 1709978 View in Reaxys 22/487 Yield 0.36 mol, 0.035 mol,

Conditions & References With 2,2,3,3-tetraphenylbutane, oxygen, Time= 48h, T= 29.9 °C , p= 304Torr , variation of reagent, pressure, reaction time, Rate constant, Product distribution

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0.0014 Howard, J. A.; Bennett, J. E.; Brunton, G.; Canadian Journal of Chemistry; vol. 59; (1981); p. 2253 - 2260 mol, View in Reaxys 0.0015 mol 7 :EXAMPLE 7A solution of 10 mL of cumene (72 mmoles), 1.44 mL of cumyl hydroperoxide and 0.72 mmoles of Nhydroxyphthalimide is stirred at 125° C. for 6 hours in under an oxygen atmosphere of 1 bar. 1H-NMR analysis of the reaction mixture showed a cumene conversion of 63percent with a selectivity in cumyl hydroperoxide of 68percent (result confirmed by iodometric titration). The main by-product is cumyl alcohol and the secondary products are acetophenone and dicumyl peroxide. The N-hydroxyphthalimide is mostly decomposed. With oxygen, 2-hydroxy-1,3-isoindolinedione, Time= 6h, T= 125 °C , p= 750.075Torr Patent; POLIMERI EUROPA S.P.A.; US2011/251436; (2011); (A1) English View in Reaxys

Rx-ID: 9647241 View in Reaxys 23/487 Yield

Conditions & References

77 %

With oxygen, mercury(II) oxide in methanol, acetonitrile, T= 25 °C , UV-irradiation Habibi, Mohammad H.; Farhadi, Saeid; Journal of Chemical Research; nb. 4; (2004); p. 296 - 297 View in Reaxys OH

n-Bu2MeMgLi

Rx-ID: 9906290 View in Reaxys 24/487 Yield

Conditions & References

78 %, 8 %

in tetrahydrofuran, Time= 5h, T= -78 °C Hatano, Manabu; Matsumura, Tokihiko; Ishihara, Kazuaki; Organic Letters; vol. 7; nb. 4; (2005); p. 573 - 576 View in Reaxys

Rx-ID: 11273703 View in Reaxys 25/487 Yield

Conditions & References With 2-hydroxy-1,3-isoindolinedione, oxygen, lithium chloride, bis(acetylacetonate)oxovanadium in acetonitrile, Time= 20h, T= 75 °C , p= 760.051Torr Figiel; Sobczak; New Journal of Chemistry; vol. 31; nb. 9; (2007); p. 1668 - 1673 View in Reaxys

(v4)

P (v4)

P Ru (v4)(v4) P (v6) P

(v4)

(v6)

(v4)

Rx-ID: 26743127 View in Reaxys 26/487 Yield 88 %, 85 %

Conditions & References With hydrogen, treatment of the complex with hydrogen (2 atm) Hartwig; Bergman; Andersen; Journal of the American Chemical Society; vol. 112; nb. 8; (1990); p. 3234 - 3236 ; (from Gmelin) View in Reaxys

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Mg Br O

Rx-ID: 715983 View in Reaxys 27/487 Yield 95 %

Conditions & References in tetrahydrofuran, Time= 0.55h, T= 20 °C , Inert atmosphere, Grignard reaction Riva; Gagliardi; Martinelli; Passarella; Vigo; Rencurosi; Tetrahedron; vol. 66; nb. 17; (2010); p. 3242 - 3247 View in Reaxys With diethyl ether, T= 10 - 15 °C , zuletzt bei Siedetemperatur Petrow; Kaplan; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; (1947); p. 295,303; ; (1949); p. 1718 View in Reaxys

O O

Rx-ID: 1709979 View in Reaxys 28/487 Yield 2%

Conditions & References With ozone in acetone, Time= 3h, T= -40 °C , Yields of byproduct given Pryor, William A.; Ohto, Norio; Church, Daniel F.; Journal of the American Chemical Society; vol. 104; nb. 21; (1982); p. 5813 - 5814 View in Reaxys

(v1)

Rx-ID: 2102426 View in Reaxys 29/487 Yield

Conditions & References With diphenylmethanol in chlorobenzene, T= 26.9 °C , other reagents, Rate constant Baignee; Howard; Scaiano; Stewart; Journal of the American Chemical Society; vol. 105; nb. 19; (1983); p. 6120 6123 View in Reaxys With methanol, T= 30 - 35 °C , Irradiation, Rate constant Banks; Scaiano; Journal of the American Chemical Society; vol. 115; nb. 14; (1993); p. 6409 - 6413 View in Reaxys With tetra-N-butylammonium borohydride in benzene, T= 24.84 °C , Kinetics Sheeller, Brad; Ingold, Keith U.; Journal of the Chemical Society. Perkin Transactions 2; nb. 4; (2001); p. 480 - 486 View in Reaxys With phenol in acetonitrile, Flash photolysis, Kinetics, Further Variations: Solvents, Reagents Koner, Apurba L.; Pischel, Uwe; Nau, Werner M.; Organic Letters; vol. 9; nb. 15; (2007); p. 2899 - 2902 View in Reaxys With 2-(3,4-dihydroxyphenyl)ethylamine hydrochloride in acetonitrile, T= 24.84 °C , Inert atmosphere, Kinetics, Mechanism, Reagent/catalyst Kawashima, Tomonori; Ohkubo, Kei; Fukuzumi, Shunichi; Journal of Physical Chemistry B; vol. 114; nb. 1; (2010); p. 675 - 680 View in Reaxys With L-dopa perchlorate in acetonitrile, T= 24.84 °C , Inert atmosphere, Kinetics, Mechanism, Reagent/catalyst

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Kawashima, Tomonori; Ohkubo, Kei; Fukuzumi, Shunichi; Journal of Physical Chemistry B; vol. 114; nb. 1; (2010); p. 675 - 680 View in Reaxys With epinephrine perchlorate in acetonitrile, T= 24.84 °C , Inert atmosphere, Kinetics, Mechanism, Reagent/catalyst Kawashima, Tomonori; Ohkubo, Kei; Fukuzumi, Shunichi; Journal of Physical Chemistry B; vol. 114; nb. 1; (2010); p. 675 - 680 View in Reaxys With (2R-trans)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol in acetonitrile, T= 24.84 °C , Inert atmosphere, Kinetics, Mechanism, Reagent/catalyst Kawashima, Tomonori; Ohkubo, Kei; Fukuzumi, Shunichi; Journal of Physical Chemistry B; vol. 114; nb. 1; (2010); p. 675 - 680 View in Reaxys With norepinephrine perchlorate in acetonitrile, T= 24.84 °C , Inert atmosphere, Kinetics, Mechanism, Reagent/catalyst Kawashima, Tomonori; Ohkubo, Kei; Fukuzumi, Shunichi; Journal of Physical Chemistry B; vol. 114; nb. 1; (2010); p. 675 - 680 View in Reaxys

Rx-ID: 3923383 View in Reaxys 30/487 Yield 8 %, 92 %

Conditions & References With sodium tetrahydroborate, (5,10,15,20-tetramesitylporphyrin)MnCl, oxygen in ethanol, benzene, Time= 0.583333h, Ambient temperature Takeuchi, Masayuki; Kano, Koji; Bulletin of the Chemical Society of Japan; vol. 67; nb. 6; (1994); p. 1726 - 1733 View in Reaxys

40 %, 41 %

With sodium tetrahydroborate, oxygen, 5,10,15,20-tetrakisphenylporphyrinatoiron(III) chloride in methanol, benzene, Ambient temperature Santa; Mori; Hirobe; Chemical and pharmaceutical bulletin; vol. 33; nb. 5; (1985); p. 2175 - 2178 View in Reaxys

41 %, 40 %

Li O

Rx-ID: 9893082 View in Reaxys 31/487 Yield 93 %, 6 %

Conditions & References Stage 1: in tetrahydrofuran, diethyl ether, Time= 1h, T= -78 °C Stage 2: in tetrahydrofuran, diethyl ether, Time= 5h, T= -78 °C Hatano, Manabu; Matsumura, Tokihiko; Ishihara, Kazuaki; Organic Letters; vol. 7; nb. 4; (2005); p. 573 - 576 View in Reaxys

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n-BuMe2MgLi

Rx-ID: 9906292 View in Reaxys 32/487 Yield

Conditions & References

72 %, 26 %

in tetrahydrofuran, Time= 5h, T= -78 °C Hatano, Manabu; Matsumura, Tokihiko; Ishihara, Kazuaki; Organic Letters; vol. 7; nb. 4; (2005); p. 573 - 576 View in Reaxys

O HO

Rx-ID: 10122143 View in Reaxys 33/487 Yield

Conditions & References

70 %

With hydrogen, palladium dihydroxide, palladium on activated charcoal in tetrahydrofuran, water, isopropyl alcohol, Time= 12h Li, Yong; Manickam, Govindaswamy; Ghoshal, Atanu; Subramaniam, Prasad; Synthetic Communications; vol. 36; nb. 7; (2006); p. 925 - 928 View in Reaxys

(v4)

P (v4) P RuP H HOC-6 (v4) (v4) (v6) P

O P Ru (v4)(v4) P (v6) P

(v4)

Rx-ID: 26743128 View in Reaxys 34/487 Yield 88 %, 84 %

Conditions & References With H2 in benzene-d6, soln. degased, submerged in liquid nitrogen and exposed to H2 (450 Torr), sealed, 2 h at 25°C; not isolated; NMR Hartwig, John F.; Bergman, Robert G.; Andersen, Richard A.; Organometallics; vol. 10; (1991); p. 3344 - 3362 ; (from Gmelin) View in Reaxys

Rx-ID: 2017888 View in Reaxys 35/487 Yield 95 %, 4 %

Conditions & References With [FeIII(5,10,15,20-meso-tetraphenylporphyrin)Cl] in cyclohexane, benzene, T= 20 °C , half life time t1/2 Mansuy, Daniel; Bartoli, Jean-Francois; Chottard, Jean-Claude; Lange, Marc; Angewandte Chemie; vol. 92; nb. 11; (1980); p. 938 - 939 View in Reaxys

93 %, 7%

With C19H19N3*Cu(1+)*C2H3N*F6P(1-) in acetonitrile, Concentration, Reagent/catalyst Tano, Tetsuro; Sugimoto, Hideki; Fujieda, Nobutaka; Itoh, Shinobu; European Journal of Inorganic Chemistry; nb. 26; (2012); p. 4099 - 4103 View in Reaxys

49 %, 45 %

With air, zinc, iron(II) chloride in pyridine, acetic acid, Time= 16h, Ambient temperature Barton; Halley; Ozbalik; Mehl; Tetrahedron Letters; vol. 30; nb. 48; (1989); p. 6615 - 6618 View in Reaxys

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45 %, 49 %

With air, zinc, iron(II) chloride in pyridine, acetic acid, Time= 16h, Ambient temperature Barton; Halley; Ozbalik; Mehl; Tetrahedron Letters; vol. 30; nb. 48; (1989); p. 6615 - 6618 View in Reaxys in cyclohexane, toluene, T= 145 °C , other temperature and solvents, solvent compositions, Mechanism, Product distribution Chodak, Ivan; Bakos, Dusan; Mihalov, Vincent; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 1457 - 1459 View in Reaxys With cyclohexane, cobalt tetra-4-tert-butylphthalocyanine in benzene, Time= 0.25h, T= 20 °C , or in presence of an inhibitor, N-phenyl-β-naphthylamine, Product distribution, Mechanism Barkanova, S. V.; Zheltukhin, I. A.; Kaliya, O. L.; Journal of Organic Chemistry USSR (English Translation); vol. 19; nb. 10; (1983); p. 1927 - 1928; Zhurnal Organicheskoi Khimii; vol. 19; nb. 10; (1983); p. 2212 - 2213 View in Reaxys With cobalt(II) 2,4-pentanedionate in chlorobenzene, T= 49.9 °C , Product distribution Howard, J. A.; Tong, S. B.; Canadian Journal of Chemistry; vol. 58; (1980); p. 1962 - 1965 View in Reaxys With copper diacetate in acetic acid, T= 60 °C , decomposition studies with copper(I)) acetate; also with LiCl; different time, Kinetics, Mechanism, Product distribution Koshitani, Jinya; Inugai, Masao; Ueno, Yoshio; Yoshida, Takatoshi; Monatshefte fuer Chemie; vol. 114; (1983); p. 1391 - 1398 View in Reaxys With Ni bis(N-benzaliminyl-o-aminobenzoate) in chlorobenzene, T= 110 °C , other catalyst, Rate constant Kovtun, G. A.; Lysenko, D. L.; Moiseev, I. I.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 32; nb. 1; (1983); p. 25 - 29; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1983); p. 35 - 40 View in Reaxys

17.35 % Chromat., 52.0 % Chromat.

With zinc phenanthroline mono in various solvent(s), Time= 2.5h, T= 130 °C , further catalysts, Product distribution Kozlov; Potekhin; Journal of applied chemistry of the USSR; vol. 59; nb. 6 pt 2; (1986); p. 1277 - 1280 View in Reaxys With potassium hydroxide in chlorobenzene, T= 343 °C , var. solvents, var. conc. of KOH, also with phenylacetylene, Mechanism, Rate constant Lyavinets, A. S.; Choban, A. F.; Chervinskii, K. A.; Petroleum Chemistry (English Translation); vol. 35; nb. 5; (1995); p. 431 - 438; Neftekhimiya; vol. 35; nb. 5; (1995); p. 448 - 454 View in Reaxys With [iron(II)(H2O)6](perchlorate)2 in pyridine, T= 25 °C , Kinetics, Product distribution Barton, Derek H. R.; Launay, Franck; Tetrahedron; vol. 53; nb. 43; (1997); p. 14565 - 14578 View in Reaxys With N -hydroxyphthalimide, oxygen, anhydrous cobalt diacetate in acetonitrile, Time= 3h, T= 25 °C , p= 760.051Torr , Decomposition, Product distribution, Further Variations: Reagents Iwahama, Takahiro; Yoshino, Yasushi; Keitoku, Takashi; Sakaguchi, Satoshi; Ishii, Yasutaka; Journal of Organic Chemistry; vol. 65; nb. 20; (2000); p. 6502 - 6507 View in Reaxys With 2,2'-azobis(isobutyronitrile), oxygen, Time= 2h, T= 90 °C , p= 9000.9Torr , Autoclave Lloyd, Rhys; Jenkins, Robert L.; Piccinini, Marco; He, Qian; Kiely, Christopher J.; Carley, Albert F.; Golunski, Stanislaw E.; Bethell, Donald; Bartley, Jonathan K.; Hutchings, Graham J.; Journal of Catalysis; vol. 283; nb. 2; (2011); p. 161 - 167

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View in Reaxys With myoglobin H64D mutant, Time= 0.0833333h, T= 25 °C , aq. buffer Matsuo, Takashi; Fukumoto, Kazuki; Watanabe, Takuro; Hayashi, Takashi; Chemistry - An Asian Journal; vol. 6; nb. 9; (2011); p. 2491 - 2499 View in Reaxys With horse heart myoglobin reconstituted with manganese porphycene, 2-methoxylphenol in aq. phosphate buffer, Time= 2h, T= 25 °C , pH= 7 Oohora, Koji; Kihira, Yushi; Mizohata, Eiichi; Inoue, Tsuyoshi; Hayashi, Takashi; Journal of the American Chemical Society; vol. 135; nb. 46; (2013); p. 17282 - 17285 View in Reaxys With C98H129CuN5 (1+)*ClO4 (1-) in acetone, Time= 5h, T= -60 °C Paria, Sayantan; Ohta, Takehiro; Morimoto, Yuma; Ogura, Takashi; Sugimoto, Hideki; Fujieda, Nobutaka; Goto, Kei; Asano, Kaori; Suzuki, Takeyuki; Itoh, Shinobu; Journal of the American Chemical Society; vol. 137; nb. 34; (2015); p. 10870 - 10873 View in Reaxys

Rx-ID: 2937644 View in Reaxys 36/487 Yield

Conditions & References

46 %

With 4,4'-di-tert-butylbiphenyl, lithium in tetrahydrofuran, Time= 0.166667h, T= -30 °C Guijarro; Yus; Tetrahedron; vol. 50; nb. 11; (1994); p. 3447 - 3452 View in Reaxys

SiH

Co(III)-cumylperoxo complex

O Si

Rx-ID: 9175871 View in Reaxys 37/487 Yield 60 %, 33 %

Conditions & References in 1,2-dichloro-ethane, Time= 2h, T= 20 °C Tokuyasu, Takahiro; Kunikawa, Shigeki; Masuyama, Araki; Nojima, Masatomo; Organic Letters; vol. 4; nb. 21; (2002); p. 3595 - 3598 View in Reaxys

OH H

O HO

Rx-ID: 23047563 View in Reaxys 38/487 Yield

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7percent O2 in N2, and a steady pressure of 40 psig.All experiments were carried out in a 500 cc Buchi Type II reactor, with a stirring rate of 1300 rpm. The foregoing stock oxidation mixture was used in a control oxidation to provide a comparative example to assess the effect of ammonia on the reaction.Neither ammonia nor water was added to the control experiment.After 8 hours, the mixture contained 340 wppm formic acid, 752 wppm acetic acid, and 515 wppm phenol. In a first comparative experiment, during the oxidation, gaseous NH3 was bubbled through the oxidation mixture at a molar ratio of 1.28 to 1 based on the expected acid production, resulting in an ammonia feed rate of 0.379 cc/min at STP. No water was added in this experiment. [0031] In a second comparative experiment, 1.25 wt. percent water was charged to the standard oxidation mixture, and during the oxidation, gaseous ammonia was bubbled through the oxidation mixture at a molar ratio of NH3 to expected acid production of 1.28 to 1, resulting in a feed rate of the aqueous ammonia of 0.375 cc/min. at STP. [0032] Measurements of cumene hydroperoxide (CHP), s-butylbenzene hydroperoxide (sBBHP), AP, DMBA, and EMBA were taken every hour, after the reaction temperature reached designed temperature and NH3 feed started. All results listed below are in percent wt: With oxygen, Time= 1 - 8h, T= 130 °C , p= 2068.65Torr Patent; Yang, Jiemin; Black, Jesse Raymond; US2004/162448; (2004); (A1) English View in Reaxys

Rx-ID: 23827589 View in Reaxys 39/487 Yield

Conditions & References 1; 2 :Example 1; Cumene recycled from a hydrogenation step was mixed with an aqueous solution of 1.5 wt.percent of sodium carbonate in a weight ratio of 1 of the aqueous solution to 20 of cumene, and the mixture was reacted under a pressure of 630 kPa and a temperature of 90 to 105°C for of 5 hours supplying air. At this time, a concentration of 1,2-epoxy-2-phenylpropane was 0.2percent by weight. A formed oxidized liquid had the following composition.; A reaction operation was carried out in the same manner as in Example 1 except that the lot of cumene recycled from the hydrogenation step, was changed. At this time, a concentration of 1,2-epoxy-2-phenylpropane was 0.6percent by weight. A formed oxidized liquid had the following composition.; A reaction operation was carried out in the same manner as in Example 1 except that the lot of cumene recycled from the hydrogenation step, was changed. At this time, a concentration of 1,2-epoxy-2-phenylpropane was 1.5percent by weight. A formed oxidized liquid had the following composition. With oxygen, sodium carbonate in water, Time= 5h, T= 90 - 105 °C , p= 4725.47Torr , Product distribution / selectivity Patent; Sumitomo Chemical Company, Limited; EP1681288; (2006); (A1) English View in Reaxys

O HO

Rx-ID: 32321668 View in Reaxys 40/487 Yield

Conditions & References

80 %

With potassium fluoride, tetraethylene glycol, Time= 20h, T= 20 °C Yan, Hailong; Oh, Joong-Suk; Song, Choong Eui; Organic and Biomolecular Chemistry; vol. 9; nb. 23; (2011); p. 8119 - 8121 View in Reaxys

Li O

Rx-ID: 3383137 View in Reaxys 41/487 Yield 96 %

Conditions & References With cerium(III) iodide in tetrahydrofuran, hexane, Time= 3h, T= -65 °C , var. temp., time; also without CeI3, Product distribution

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Imamoto, Tsuneo; Kusumoto, Tetsuo; Yokoyama, Masataka; Journal of the Chemical Society, Chemical Communications; nb. 18; (1982); p. 1042 - 1044 View in Reaxys 96 %

With cerium(III) iodide in tetrahydrofuran, hexane, Time= 3h, T= -65 °C Imamoto, Tsuneo; Kusumoto, Tetsuo; Yokoyama, Masataka; Journal of the Chemical Society, Chemical Communications; nb. 18; (1982); p. 1042 - 1044 View in Reaxys

95 %

With Chromium (III) chloride in tetrahydrofuran Eisch, John J.; Shi, Xian; Alila, Joseph R.; Thiele, Sven; Chemische Berichte; vol. 130; nb. 9; (1997); p. 1175 1187 View in Reaxys With lanthanum trifluoromethanesulphonate, THF, -78 deg C, N,N-diethyl-p-toluamide, Yield given. Multistep reaction Collins, Scott; Hong, Yaping; Tetrahedron Letters; vol. 28; nb. 38; (1987); p. 4391 - 4394 View in Reaxys With cerium(III) iodide, in THF, 1) -65 deg C, 30 min., 2) -65 deg C, 3h, Yield given. Multistep reaction Imamoto, Tsuneo; Kusumoto, Tetsuo; Tawarayama, Yoshinori; Sugiura, Yasushi; Mita, Takeshi; et al.; Journal of Organic Chemistry; vol. 49; nb. 21; (1984); p. 3904 - 3912 View in Reaxys

O N

H N

O N

Rx-ID: 3779732 View in Reaxys 42/487 Yield 57.0 %

Conditions & References With TPP(Cl)MnIIIImH in dichloromethane, T= 25 °C , Rate constant Yuan, Lung-Chi; Bruice, Thomas C.; Journal of the American Chemical Society; vol. 108; nb. 7; (1986); p. 1643 1650 View in Reaxys

57.0 %

With TPPMnIII(ImH)2Cl in dichloromethane, T= 25 °C , Rate constant Yuan, Lung-Chi; Bruice, Thomas C.; Journal of the American Chemical Society; vol. 108; nb. 7; (1986); p. 1643 1650 View in Reaxys

Rx-ID: 3923387 View in Reaxys 43/487 Yield

Conditions & References With sodium hydroxide, bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate, dihydrogen peroxide, 1,4-di(diphenylphosphino)-butane, benzo[1,3,2]dioxaborole, 1.) THF, 25 deg C, 15 h, 2.) THF, RT, 3 h, Yield given. Multistep reaction. Yields of byproduct given Hayashi; Matsumoto; Ito; Tetrahedron Asymmetry; vol. 2; nb. 7; (1991); p. 601 - 612 View in Reaxys With sodium hydroxide, bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate, dihydrogen peroxide, 1,4-di(diphenylphosphino)-butane, benzo[1,3,2]dioxaborole, 1.) THF, 25 deg C, 0.5 h, 2.) THF, RT, 3 h, Yield given. Multistep reaction. Yields of byproduct given

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Hayashi; Matsumoto; Ito; Tetrahedron Asymmetry; vol. 2; nb. 7; (1991); p. 601 - 612 View in Reaxys Stage 1: With dioxane-BH2Cl in 1,4-dioxane, T= 20 °C Stage 2: With sodium hydroxide, dihydrogen peroxide in methanol, water, T= 20 - 40 °C , Further stages. Kanth; Brown; Journal of Organic Chemistry; vol. 66; nb. 16; (2001); p. 5359 - 5365 View in Reaxys

O O

Rx-ID: 3943885 View in Reaxys 44/487 Yield

Conditions & References

49 %, 3 %, With cerium, iodine, methyl iodide in tetrahydrofuran, Time= 3h, T= -20 °C 3% Fukuzawa, Shin-ichi; Fujinami, Tatsuo; Sakai, Shizuyoshi; Journal of Organometallic Chemistry; vol. 299; (1986); p. 179 - 186 View in Reaxys

Rx-ID: 5053130 View in Reaxys 45/487 Yield

Conditions & References

90 %, 40 %, 4 %, 3 %

Time= 3h, T= 69 °C , Decomposition, Further byproducts given Dolenc, Darko; Plesnicar, Bozo; Journal of the American Chemical Society; vol. 119; nb. 11; (1997); p. 2628 2632 View in Reaxys

Cl I

HSO2H

O HO

Rx-ID: 16554697 View in Reaxys 46/487 Yield

Conditions & References Reaction Steps: 3 1: 50 percent / potassium tert-butoxide / tetrahydrofuran / cooling 2: 26 percent / benzene-d6 / 3 h / 69 °C 3: di-tert-butylperoxyoxalate / 2 h / Heating With (tBuOOCO)2, potassium tert-butylate in tetrahydrofuran, benzene-d6, 1: alkylperoxidation / 2: Decomposition / 3: deiodination Dolenc, Darko; Plesnicar, Bozo; Journal of the American Chemical Society; vol. 119; nb. 11; (1997); p. 2628 2632 View in Reaxys Reaction Steps: 4 1: 50 percent / potassium tert-butoxide / tetrahydrofuran / cooling 2: 26 percent / benzene-d6 / 3 h / 69 °C 3: deuterium oxide / cyclohexane / 0.5 h / ultrasound 4: di-tert-butylperoxyoxalate / 2 h / Heating With (tBuOOCO)2, potassium tert-butylate, water-d2 in tetrahydrofuran, cyclohexane, benzene-d6, 1: alkylperoxidation / 2: Decomposition / 3: deuteration / 4: deiodination Dolenc, Darko; Plesnicar, Bozo; Journal of the American Chemical Society; vol. 119; nb. 11; (1997); p. 2628 2632

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View in Reaxys

HSO2H

Rx-ID: 16579733 View in Reaxys 47/487 Yield

Conditions & References Reaction Steps: 2 1: 26 percent / benzene-d6 / 3 h / 69 °C 2: di-tert-butylperoxyoxalate / 2 h / Heating With (tBuOOCO)2 in benzene-d6, 1: Decomposition / 2: deiodination Dolenc, Darko; Plesnicar, Bozo; Journal of the American Chemical Society; vol. 119; nb. 11; (1997); p. 2628 2632 View in Reaxys Reaction Steps: 3 1: 26 percent / benzene-d6 / 3 h / 69 °C 2: deuterium oxide / cyclohexane / 0.5 h / ultrasound 3: di-tert-butylperoxyoxalate / 2 h / Heating With (tBuOOCO)2, water-d2 in cyclohexane, benzene-d6, 1: Decomposition / 2: deuteration / 3: deiodination Dolenc, Darko; Plesnicar, Bozo; Journal of the American Chemical Society; vol. 119; nb. 11; (1997); p. 2628 2632 View in Reaxys O O O

Rx-ID: 2018130 View in Reaxys 48/487 Yield

Conditions & References

79 %, 9 %

With Me4CoLi2 in diethyl ether, Time= 18h, -78 deg C to r.t. Kauffmann, Thomas; Hopp, Gudrun; Laarmann, Barbara; Stegemann, Dieter; Wingbermuehle, Dorothea; Tetrahedron Letters; vol. 31; nb. 4; (1990); p. 511 - 514 View in Reaxys O

Rx-ID: 4579344 View in Reaxys 49/487 Yield

Conditions & References

33 %

With naphthalene, lithium in tetrahydrofuran, Time= 2h, T= -78 - 0 °C Alonso, Emma; Ramon, Diego J.; Yus, Miguel; Tetrahedron; vol. 52; nb. 45; (1996); p. 14341 - 14348 View in Reaxys

O O

Me2CuLi

Rx-ID: 5930488 View in Reaxys 50/487 Yield 8 % Chromat., 10 % Chromat.

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View in Reaxys 10 % Chromat., 8 % Chromat.

in tetrahydrofuran, Time= 0.5h, T= -78 °C , Title compound not separated from byproducts Lipshutz, Bruce H.; Kozlowski, Joseph A.; Breneman, Curt M.; Journal of the American Chemical Society; vol. 107; nb. 11; (1985); p. 3197 - 3204 View in Reaxys

Rx-ID: 10122382 View in Reaxys 51/487 Yield

Conditions & References

28 % Spectr., 14 % Spectr.

With 5-methoxy-phenanthridinium in acetonitrile-D3, T= 25 °C , Irradiation Baciocchi, Enrico; Del Giacco, Tiziana; Gerini, Maria Francesca; Lanzalunga, Osvaldo; Organic Letters; vol. 8; nb. 4; (2006); p. 641 - 644 View in Reaxys

Rx-ID: 14216492 View in Reaxys 52/487 Yield

Conditions & References Reaction Steps: 2 1: O2; α-tocopherol / benzene / Photolysis 2: PPh3; BHT / benzene With 2,6-di-tert-butyl-4-methyl-phenol, oxygen, triphenylphosphine, 2,5,7,8-tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanol in benzene Pratt, Derek A.; Mills, Jeremy H.; Porter, Ned A.; Journal of the American Chemical Society; vol. 125; nb. 19; (2003); p. 5801 - 5810 View in Reaxys I

HSO2H HO

Rx-ID: 16561516 View in Reaxys 53/487 Yield

Conditions & References Reaction Steps: 2 1: deuterium oxide / cyclohexane / 0.5 h / ultrasound 2: di-tert-butylperoxyoxalate / 2 h / Heating With (tBuOOCO)2, water-d2 in cyclohexane, 1: deuteration / 2: deiodination Dolenc, Darko; Plesnicar, Bozo; Journal of the American Chemical Society; vol. 119; nb. 11; (1997); p. 2628 2632 View in Reaxys

Rx-ID: 22961796 View in Reaxys 54/487 Yield

Conditions & References The second step is a step of reacting cumene hydroperoxide obtained in the first step with propylene to obtain propylene oxide and cumyl alcohol. The epoxidation catalyst is preferably a catalyst containing a titanium-containing sili-

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con oxide from the viewpoint of obtaining the objective product under high yield and high selectivity. As these catalysts, so-called Ti-silica catalysts containing Ti chemically bonded to silicon oxide are preferable. For example, a catalyst prepared by supporting a Ti compound on a silica carrier, a catalyst prepared by combining a Ti compound with silicon oxide by a co-precipitation method or sol-gel method, zeolite compounds containing Ti, and the like are listed. The epoxidation is conducted by contacting propylene and cumene hydroperoxide with the catalyst. The reaction can be carried out in a liquid phase using a solvent. The solvent must be liquid under temperature and pressure in the reaction, and substantially inert to reactants and products. The solvent may be that which is composed of a substance present in a hydroperoxide solution used. For example, when cumene hydroperoxide is a mixture with cumene which is a raw material therefor, this can be also used instead of a solvent without particularly adding a solvent. Additionally, monocyclic aromatic compounds (e.g. benzene, toluene, chlorobenzene, orthodichlorobenzene), and alkanes (e.g. octane, decane, dodecane) and the like are listed as useful solvents. The epoxidation temperature is usually from 0 to 200°C, and preferably from 25 to 200°C. The pressure may be at a level sufficient to keep the reaction mixture in a liquid condition. In general, the pressure is advantageously from 100 to 10000 kPa. The epoxidation can be carried out advantageously using a catalyst in the form of a slurry or fixed bed. In the case of a large scale industrial operation, a fixed bed is preferably used. The epoxidation can be conducted by a batch-wise method, semi-continuous method, continuous method or the like. When liquid containing raw materials for reaction is passed through a fixed bed, a liquid-like mixture discharged from a reaction region does not contain a catalyst at all or contains substantially no catalyst. With titanium-containing silicon oxide, T= 25 - 200 °C , p= 750.075 - 75007.5Torr , Industry scale Patent; Sumitomo Chemical Company, Limited; EP1420014; (2004); (A1) English View in Reaxys 3 :Example 3According to the method described in the specification as schematically shown in FIG. 3, using cumene as the alkylbenzene, an oxidation reaction liquid (101) containing 25percent to 30percent by weight of cumene hydroperoxide was obtained by oxidizing cumene with air in the oxidation step. An epoxidation reaction liquid (102) containing mainly propylene oxide, cumyl alcohol, unreacted propylene, and cumene was obtained by passing the oxidation reaction liquid and propylene through a reactor filled with a titanium-containing silicon oxide catalyst in the epoxidation step. Cumyl alcohol is an alcohol comes from the cumene hydroperoxide. The unreacted propylene (103) was separated and removed from the resulted reaction liquid (102) to obtain a reaction liquid (104) after recovering propylene. The reaction liquid (104) after recovering propylene was separated into a liquid fraction (105) containing mainly cumyl alcohol and cumene and a fraction containing mainly propylene oxide in the propylene oxide purification step, and then the fraction containing mainly propylene oxide was distilled with a plurality of distillation columns including extraction distillation so as to obtain a propylene oxide product which satisfies the product qualities. The liquid fraction (105) containing mainly cumyl alcohol and cumene as a continuous phase and a hydrogen gas as a dispersed phase was fed through the reactor in up-flow mode which was provided with i) a catalyst bed comprising an activated alumina catalyst and a palladium containing catalyst and ii) the gas-liquid dispersion device according to the present invention at the middle of the reactor, so that cumyl alcohol was reduced to cumene. The conversion of cumyl alcohol to cumene was more than 98percent. The obtained cumene was recycled to the oxidation step. FIG. 3 illustrates the schematic flow-chart of Example 3 described in the specification. With titanium-containing silicon oxide in isopropyl-benzene, the gas-liquid dispersion device, Industry scale, Product distribution / selectivity Patent; Sumitomo Chemical Company, Limited; US2011/4009; (2011); (A1) English View in Reaxys O

O HO

OH S

O N

Rx-ID: 38334280 View in Reaxys 55/487 Yield

Conditions & References Stage 1: With supramolecular artificial glutathione peroxidase (SGPxmax) in aq. phosphate buffer, Time= 0.05h, T= 36 °C , pH= 7, Enzymatic reaction Stage 2: in aq. phosphate buffer, Kinetics, Catalytic behavior, Reagent/catalyst Yin, Yanzhen; Jiao, Shufei; Lang, Chao; Liu, Junqiu; RSC Advances; vol. 4; nb. 48; (2014); p. 25040 - 25050 View in Reaxys

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Determination of glutathione peroxidase activity in solvent mixture of PBS and co-solvents The catalytic activity was assayed according to a modified method reported by Hilvert and Wu[11]. The typical assay process of glutathione peroxidase activity in solvent mixture of PBS and ethanol was shown as follows: The reaction was carried out at 25 °C in a 1 mL quartz cuvette, 700 μL solvent mixture of PBS and ethanol and 100 μL of ADA-TeOH (0.025 mM) were added and then 100 μL of the 3-carboxyl-4-nitrobenzenethiol solution(1 mM) was added. The mixture in the quartz cuvette was preincubated at the 25 °C for 3 min. Finally, the reaction was initiated by the addition of 100 mL of hydroperoxide (2 mM) and the absorption decrease of 3-carboxyl-4-nitrobenzenethiol at 410 nm (ε410 = 13600 M-1 cm-1. pH = 7.0) was monitored using a Shimadzu 2600 UV-visible-NIR spectrophotometer. Appropriate control of the non-enzymatic reaction was performed and was subtracted from the catalyzed reaction. The glutathione peroxidase activities in solvent mixture of PBS and other co-solvents were assayed similarly except ethanol was replaced by other co-solvents. With C17H28O3Te in aq. phosphate buffer, ethanol, T= 25 °C , pH= 7, Kinetics, Solvent Jiao; Yin; Zhang; Zhong; Wang; Yang; Asian Journal of Chemistry; vol. 27; nb. 7; (2015); p. 2665 - 2668 View in Reaxys

O HO

Rx-ID: 2065384 View in Reaxys 56/487 Yield

Conditions & References

73 % Chromat.

With lithium in tetrahydrofuran, Time= 24h, T= 20 °C Azzena, Ugo; Denurra, Teresa; Melloni, Giovanni; Piroddi, Anna Maria; Journal of Organic Chemistry; vol. 55; nb. 20; (1990); p. 5532 - 5535 View in Reaxys

Rx-ID: 2077325 View in Reaxys 57/487 Yield

Conditions & References T= 20 °C , p= 45003600Torr , effect of shear deformation; activation energy, volume effect of activation; other temperatures, pressures, Product distribution, Thermodynamic data Dyatlov, A. I.; Zharov, A. A.; Zhulin, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 35; nb. 5; (1986); p. 932 - 935; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 5; (1986); p. 1028 - 1031 View in Reaxys Stage 1: With gold in water, T= 500 °C , Irradiation Stage 2: With methanol in water Fasciani, Chiara; Alejo, Carlos J. Bueno; Grenier, Michel; Netto-Ferreira, Jose Carlos; Scaiano; Organic Letters; vol. 13; nb. 2; (2011); p. 204 - 207 View in Reaxys With cyclohexa-1,4-diene in 2,2,2-trifluoroethanol, T= 25 °C , Flash photolysis, Inert atmosphere, Kinetics, Solvent, Concentration Salamone, Michela; Giammarioli, Ilaria; Bietti, Massimo; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4645 - 4651 View in Reaxys Reaction Steps: 2 1: acetonitrile / 25 °C / Inert atmosphere; Flash photolysis 2: acetonitrile / 25 °C / Inert atmosphere; Flash photolysis in acetonitrile

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Salamone, Michela; Dilabio, Gino A.; Bietti, Massimo; Journal of Organic Chemistry; vol. 76; nb. 15; (2011); p. 6264 - 6270 View in Reaxys Reaction Steps: 2 1: acetonitrile / 25 °C / Inert atmosphere; Flash photolysis 2: acetonitrile / 25 °C / Inert atmosphere; Flash photolysis in acetonitrile Salamone, Michela; Dilabio, Gino A.; Bietti, Massimo; Journal of Organic Chemistry; vol. 76; nb. 15; (2011); p. 6264 - 6270 View in Reaxys With N,N-dimethyl-formamide in acetonitrile, T= 25 °C , Flash photolysis, Inert atmosphere, Kinetics, Reagent/catalyst Salamone, Michela; Milan, Michela; Dilabio, Gino A.; Bietti, Massimo; Journal of Organic Chemistry; vol. 78; nb. 12; (2013); p. 5909 - 5917 View in Reaxys Stage 1: in acetonitrile, T= 25 °C , Inert atmosphere, Photolysis Stage 2: With anhydrous N,N-diethylformamide in acetonitrile, T= 25 °C , Inert atmosphere, Kinetics, Reagent/catalyst Salamone, Michela; Milan, Michela; Dilabio, Gino A.; Bietti, Massimo; Journal of Organic Chemistry; vol. 79; nb. 15; (2014); p. 7179 - 7184 View in Reaxys

N NH 2

Rx-ID: 3591669 View in Reaxys 58/487 Yield

Conditions & References With methyllithium in diethyl ether, water Lee, Soon W.; Miller, Glenn A.; Campana, Charles F.; Maciejewski, Mary L.; Trogler, William C.; Journal of the American Chemical Society; vol. 109; nb. 16; (1987); p. 5050 - 5051 View in Reaxys

Co(acac)2(py)(OOcumyl) HO

Rx-ID: 9991030 View in Reaxys 59/487 Yield 54 %

Conditions & References With phenyl silane in 1,2-dichloro-ethane, Time= 2h Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys

Co(acac)2(py)(OOcumyl) HO

Rx-ID: 9991031 View in Reaxys 60/487 Yield 58 %, 37 %

Conditions & References With triphenyl silane in 1,2-dichloro-ethane, Time= 2h Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys

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Rx-ID: 33210754 View in Reaxys 61/487 Yield

Conditions & References

92 %, 21 %

With 1-methyl-1H-imidazol-1-ium; sulfuric acid, Time= 0.05h, T= 120 °C , Microwave irradiation, chemoselective reaction Mohammadpoor-Baltork, Iraj; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Khosropour, Ahmad Reza; Mirjafari, Arsalan; Monatshefte fur Chemie; vol. 141; nb. 10; (2010); p. 1083 - 1088 View in Reaxys

O HO

Rx-ID: 33210756 View in Reaxys 62/487 Yield

Conditions & References

90 %, 13 %

With 1-methyl-1H-imidazol-1-ium; sulfuric acid, Time= 1h, T= 50 °C , chemoselective reaction Mohammadpoor-Baltork, Iraj; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Khosropour, Ahmad Reza; Mirjafari, Arsalan; Monatshefte fur Chemie; vol. 141; nb. 10; (2010); p. 1083 - 1088 View in Reaxys

Rx-ID: 33210757 View in Reaxys 63/487 Yield 92 %, 18 %

Conditions & References With 1-methyl-1H-imidazol-1-ium; sulfuric acid, Time= 0.05h, T= 120 °C , Microwave irradiation, chemoselective reaction Mohammadpoor-Baltork, Iraj; Moghadam, Majid; Tangestaninejad, Shahram; Mirkhani, Valiollah; Khosropour, Ahmad Reza; Mirjafari, Arsalan; Monatshefte fur Chemie; vol. 141; nb. 10; (2010); p. 1083 - 1088 View in Reaxys

Rx-ID: 4511327 View in Reaxys 64/487 Yield

Conditions & References

10 % Turn- With 2-hydroxy-1,3-isoindolinedione, oxygen, cobalt(II) 2,4-pentanedionate in acetic acid, Time= 6h, T= 100 °C ov., 54 % Turnov., 17 Ishii, Yasutaka; Iwahama, Takahiro; Sakaguchi, Satoshi; Nakayama, Kouichi; Nishiyama, Yutaka; Journal of % Turnov. Organic Chemistry; vol. 61; nb. 14; (1996); p. 4520 - 4526 View in Reaxys 17 % Turn- With 2-hydroxy-1,3-isoindolinedione, oxygen, cobalt(II) 2,4-pentanedionate in acetic acid, Time= 6h, T= 100 °C ov., 54 % Turnov., 10 Ishii, Yasutaka; Iwahama, Takahiro; Sakaguchi, Satoshi; Nakayama, Kouichi; Nishiyama, Yutaka; Journal of % Turnov. Organic Chemistry; vol. 61; nb. 14; (1996); p. 4520 - 4526 View in Reaxys

Rx-ID: 9062270 View in Reaxys 65/487

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Yield

Conditions & References

55 %, 28 %, 13 %

With 2-hydroxy-1,3-isoindolinedione, air, nitrogen(IV) oxide, Time= 5h, T= 70 °C Nishiwaki, Yoshiki; Sakaguchi, Satoshi; Ishii, Yasutaka; Journal of Organic Chemistry; vol. 67; nb. 16; (2002); p. 5663 - 5668 View in Reaxys

SiH HO

Rx-ID: 12957262 View in Reaxys 66/487 Yield

Conditions & References Reaction Steps: 3 1: 18 percent / 1,2-dichloro-ethane / 2 h 2: 23 percent / triethylamine / hexane / 10 h / 0 °C 3: 38 percent / silica gel / diethyl ether; hexane With silica gel, triethylamine in diethyl ether, hexane, 1,2-dichloro-ethane Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys Reaction Steps: 2 1: 18 percent / 1,2-dichloro-ethane / 2 h 2: 72 percent / PhSiH3; oxygen / Co(5,5-dimethyl-1-morpholin-4-yl-hexane-1,2,4-trionato)2 / 1,2-dichloro-ethane / 4 h / 20 °C With phenyl silane, oxygen, Co(modp)2 in 1,2-dichloro-ethane Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys

SiH

Rx-ID: 12959373 View in Reaxys 67/487 Yield

Conditions & References Reaction Steps: 3 1: 5 percent / 1,2-dichloro-ethane / 2 h / 20 °C 2: 23 percent / triethylamine / hexane / 10 h / 0 °C 3: 38 percent / silica gel / diethyl ether; hexane With silica gel, triethylamine in diethyl ether, hexane, 1,2-dichloro-ethane Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys Reaction Steps: 2 1: 5 percent / 1,2-dichloro-ethane / 2 h / 20 °C 2: 72 percent / PhSiH3; oxygen / Co(5,5-dimethyl-1-morpholin-4-yl-hexane-1,2,4-trionato)2 / 1,2-dichloro-ethane / 4 h / 20 °C With phenyl silane, oxygen, Co(modp)2 in 1,2-dichloro-ethane Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys

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Rx-ID: 31042377 View in Reaxys 68/487 Yield

Conditions & References

56 %Chromat., 7 %Chromat., 6 %Chromat.

With oxygen in acetonitrile, T= 150 °C , p= 7500.75Torr , Autoclave, chemoselective reaction Li, Xin-Hao; Chen, Jie-Sheng; Wang, Xinchen; Sun, Jianhua; Antonietti, Markus; Journal of the American Chemical Society; vol. 133; nb. 21; (2011); p. 8074 - 8077 View in Reaxys

(v4)

+Cu S (v4) H N (v4) O O

N (v4)

2+Cu

(v4) S

(v4)

Rx-ID: 37448524 View in Reaxys 69/487 Yield 98 %

Conditions & References in acetone, Time= 1h, T= -85 °C Tano, Tetsuro; Mieda, Kaoru; Sugimoto, Hideki; Ogura, Takashi; Itoh, Shinobu; Dalton Transactions; vol. 43; nb. 12; (2014); p. 4871 - 4877 View in Reaxys

O Br–+Mg

Rx-ID: 744795 View in Reaxys 70/487 Yield 85 %

Conditions & References Stage 1: in tetrahydrofuran Stage 2:Time= 3h, Further stages. Ramnial, Taramatee; Taylor, Stephanie A.; Bender, Marissa L.; Gorodetsky, Brian; Lee, Peter T. K.; Dickie, Diane A.; McCollum, Brett M.; Pye, Cory C.; Walsby, Charles J.; Clyburne, Jason A. C.; Journal of Organic Chemistry; vol. 73; nb. 3; (2008); p. 801 - 812 View in Reaxys

82 %

With Cyphos® IL 101 Ramnial, Taramatee; Ino, Daisuke D.; Clyburne, Jason A. C.; Chemical Communications; nb. 3; (2005); p. 325 327 View in Reaxys in diethyl ether, T= 20 °C , Rate constant Holm, Torkil; Acta Chemica Scandinavica; vol. 45; nb. 9; (1991); p. 925 - 929 View in Reaxys With diethyl ether, Zersetzung des Reaktionsproduktes durch Eiswasser Tissier; Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 1184 View in Reaxys With bis(cyclopentadienyl)titanium dichloride in diethyl ether, Time= 0.333333h, Yield given Sato, Fumie; Jinbo, Takamasa; Sato, Masao; Tetrahedron Letters; vol. 21; nb. 22; (1980); p. 2171 - 2174 View in Reaxys Servis,K.L.; Shue,F.F.; Journal of the American Chemical Society; vol. 102; (1980); p. 7233 View in Reaxys

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Terao, Yoshito; Wakui, Hiroyuki; Nomoto, Michiyo; Satoh, Tetsuya; Miura, Masahiro; Nomura, Masakatsu; Journal of Organic Chemistry; vol. 68; nb. 13; (2003); p. 5236 - 5243 View in Reaxys Tissier; Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 1184 View in Reaxys

Rx-ID: 2071792 View in Reaxys 71/487 Yield

Conditions & References

29 %, 30 %, 26 %, 23 %, 33 %

With trimethylhexadecylammonium chloride, copper dichloride in water, T= 20 - 25 °C , Irradiation, cage effect, Quantum yield, Product distribution Turro, Nicholas J.; Mattay, Jochen; Journal of the American Chemical Society; vol. 103; nb. 14; (1981); p. 4200 4204 View in Reaxys With copper dichloride in water, Irradiation, micellar cage effects investigated, Product distribution Turro, J. Nicholas; Mattay, Jochen; Tetrahedron Letters; vol. 21; nb. 19; (1980); p. 1799 - 1802 View in Reaxys

O Li

Rx-ID: 3551778 View in Reaxys 72/487 Yield

Conditions & References With chloro-trimethyl-silane in tetrahydrofuran, diethyl ether, Time= 2h, T= 0 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Rubottom, George M.; Kim, Chong-wan; Journal of Organic Chemistry; vol. 48; nb. 9; (1983); p. 1550 - 1552 View in Reaxys

Rx-ID: 4668208 View in Reaxys 73/487 Yield

Conditions & References

54 %, 6 %, With C28H26N6ORu(2+)*3F6P(1-)*H(1+) in acetonitrile-D3, T= 24.84 °C , Inert atmosphere, Kinetics 6% Kojima, Takahiko; Nakayama, Kazuya; Ikemura, Kenichiro; Ogura, Takashi; Fukuzumi, Shunichi; Journal of the American Chemical Society; vol. 133; nb. 30; (2011); p. 11692 - 11700 View in Reaxys 15 %, 13 %, 34 %

With C16H10Br4CoN2O2, oxygen, T= 60 °C , Inert atmosphere, Neat (no solvent) Ghanbari; Ferdosi; Tafazolian; Research on Chemical Intermediates; vol. 38; nb. 3-5; (2012); p. 871 - 883 View in Reaxys With lt;Fe2(μ-O)2(TPA)2gt;3+ in acetonitrile, T= -40 °C , Yield given. Yields of byproduct given Kim; Dong; Que L.; Journal of the American Chemical Society; vol. 119; nb. 15; (1997); p. 3635 - 3636 View in Reaxys

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Rx-ID: 5188550 View in Reaxys 74/487 Yield

Conditions & References

63 %

With tetrabutylammomium bromide, sodium chloride, Time= 3h, T= 70 °C , Oxidation Zawadiak, Jan; Gilner, Danuta; Mazurkiewicz, Roman; Tetrahedron Letters; vol. 40; nb. 21; (1999); p. 4059 4062 View in Reaxys

O SiH

Rx-ID: 9978570 View in Reaxys 75/487 Yield

Conditions & References

49 %, 38 %

With silica gel in diethyl ether, hexane Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys

O SiH

Rx-ID: 12968823 View in Reaxys 76/487 Yield

Conditions & References Reaction Steps: 2 1: 49 percent / silica gel / diethyl ether; hexane 2: 72 percent / PhSiH3; oxygen / Co(5,5-dimethyl-1-morpholin-4-yl-hexane-1,2,4-trionato)2 / 1,2-dichloro-ethane / 4 h / 20 °C With phenyl silane, oxygen, silica gel, Co(modp)2 in diethyl ether, hexane, 1,2-dichloro-ethane Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys

Rx-ID: 30448658 View in Reaxys 77/487 Yield

Conditions & References With 3-chloro-benzenecarboperoxoic acid, iron(II) chloride in acetonitrile, Time= 1h, T= 23 °C , Inert atmosphere Goldsmith, Christian R.; Coates, Cristina M.; Hagan, Kenton; Mitchell, Casey A.; Journal of Molecular Catalysis A: Chemical; vol. 335; nb. 1-2; (2011); p. 24 - 30 View in Reaxys

Rx-ID: 38846036 View in Reaxys 78/487

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Yield

Conditions & References 4.8.1. General method General procedure: To a solution of vanadium catalyst in chloroform (1.5 mL) was added cumene hydroperoxide (80 percent by weight). The mixture was heated for 1 min to 60oC and treated ata temperature of 20oC with chloroform (1.5 mL). The reaction mixture was stirred 72oh at 20oC and filtrated through a pad of neutral aluminum oxide. Lipophilic products were washed with ethyl acetate (5mL) from the pad of aluminum oxide. The eluate wa streated with triphenylphosphine and the solution stirred for 5 min. With [VO(N-salicylidene 2-aminophenolate)(OEt)]EtOH in chloroform, Time= 72h, T= 20 - 60 °C , Catalytic behavior, Reagent/catalyst Amberg, Matthias; Dönges, Maike; Stapf, Georg; Hartung, Jens; Tetrahedron; vol. 70; nb. 34; (2014); p. 5321 5331 View in Reaxys

I Cl

Rx-ID: 609457 View in Reaxys 79/487 Yield

Conditions & References Tissier; Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 685 View in Reaxys Stage 1: in diethyl ether, Time= 3h, T= 25 °C , Reflux, Grignard reaction Stage 2: With sulfuric acid, water in diethyl ether, Cooling with ice Prusek, Ondrej; Bures, Filip; Pytela, Oldrich; Collection of Czechoslovak Chemical Communications; vol. 74; nb. 1; (2009); p. 85 - 99 View in Reaxys

Rx-ID: 1709954 View in Reaxys 80/487 Yield 71 %, 12 %

Conditions & References With sodium tetrahydroborate, tetreamethyl ammonium hydroxide, oxygen, polymer 1-A in methanol, Time= 1h, various catalysts, Product distribution Mori, Takashi; Santa, Tomofumi; Hirobe, Masaaki; Tetrahedron Letters; vol. 26; nb. 45; (1985); p. 5555 - 5558 View in Reaxys

12 %, 71 %

With sodium tetrahydroborate, tetreamethyl ammonium hydroxide, oxygen, polymer 1-A in methanol, Time= 1h Mori, Takashi; Santa, Tomofumi; Hirobe, Masaaki; Tetrahedron Letters; vol. 26; nb. 45; (1985); p. 5555 - 5558 View in Reaxys

41 %, 46 %

With sodium tetrahydroborate, tetreamethyl ammonium hydroxide, oxygen, (5-p-acetamidophenyl-10,15,20-triphenylporphinato)iron(III) chloride in methanol, Time= 1h Mori, Takashi; Santa, Tomofumi; Hirobe, Masaaki; Tetrahedron Letters; vol. 26; nb. 45; (1985); p. 5555 - 5558 View in Reaxys

Rx-ID: 1709982 View in Reaxys 81/487 Yield

Conditions & References With (NH4)2S2O8, copper diacetate in water, acetic acid, T= 100 °C , Yield given. Further byproducts given. Yields of byproduct given

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Walling, Cheves; Zhao, Chengxue; El-Taliawi, Gamil M.; Journal of Organic Chemistry; vol. 48; nb. 25; (1983); p. 4910 - 4914 View in Reaxys

Rx-ID: 1981278 View in Reaxys 82/487 Yield 85 %

Conditions & References With zinc oxide in water, acetone, Time= 4h, Heating Gurudutt, K. N.; Rao, L. Jagan Mohan; Rao, Sanjay; Srinivas, P.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 32; nb. 4; (1993); p. 468 - 470 View in Reaxys With water in acetone, Rate constant Litvinenko, L. M.; Benndorf, V.; Popova, R. S.; Popov, A. F.; Tormosin, I. I.; Journal of Organic Chemistry USSR (English Translation); vol. 19; nb. 4; (1983); p. 680 - 683; Zhurnal Organicheskoi Khimii; vol. 19; nb. 4; (1983); p. 772 - 775 View in Reaxys in ethanol, T= 25 °C , solvolysis with other solvents, Rate constant Liu, Kwang-Ting; Chen, Pang-Shao; Chiu, Pao-Feng; Tsao, Meng-Lin; Tetrahedron Letters; vol. 33; nb. 43; (1992); p. 6499 - 6502 View in Reaxys With acetone, T= 25 °C , Rate constant Fujio, Mizue; Nomura, Hideyuki; Nakata, Kazuhide; Saeki, Yoshihiro; Mishima, Masaaki; Kobayashi, Shinjiro; Matsushita, Toshio; Nishomoto, Kichisuke; Tsuno, Yuho; Tetrahedron Letters; vol. 35; nb. 28; (1994); p. 5005 5008 View in Reaxys

(v1)

Rx-ID: 2102428 View in Reaxys 83/487 Yield

Conditions & References With isopropyl-benzene in chlorobenzene, T= 29.9 °C , temperature dependence of product yields; relative rate constants, Product distribution Baignee; Howard; Scaiano; Stewart; Journal of the American Chemical Society; vol. 105; nb. 19; (1983); p. 6120 6123 View in Reaxys With 2-hydroxy-1,3-isoindolinedione in benzene, Time= 336h, T= 30 °C , Kinetics, Product distribution Coseri, Sergiu; Mendenhall, G. David; Ingold; Journal of Organic Chemistry; vol. 70; nb. 12; (2005); p. 4629 4636 View in Reaxys

O HO

Rx-ID: 2297353 View in Reaxys 84/487 Yield 100 % Spectr., 20 % Spectr.,

Conditions & References With para-dicyanobenzene, oxygen in tetrahydrofuran, methanol, T= 22 °C , Irradiation Maslak, Przemyslaw; Chapman Jr., William H.; Tetrahedron; vol. 46; nb. 8; (1990); p. 2715 - 2724

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78 % Spectr.

View in Reaxys

100 % Spectr., 78 % Spectr., 20 % Spectr.

With para-dicyanobenzene, oxygen in tetrahydrofuran, methanol, T= 22 °C , Irradiation Maslak, Przemyslaw; Chapman Jr., William H.; Tetrahedron; vol. 46; nb. 8; (1990); p. 2715 - 2724 View in Reaxys

I O

Rx-ID: 4031520 View in Reaxys 85/487 Yield

Conditions & References

3 %, 46 %

With cerium, iodine in tetrahydrofuran, Time= 3h, T= -20 °C Fukuzawa, Shin-ichi; Fujinami, Tatsuo; Sakai, Shizuyoshi; Journal of Organometallic Chemistry; vol. 299; (1986); p. 179 - 186 View in Reaxys

Rx-ID: 4033059 View in Reaxys 86/487 Yield

Conditions & References

53 %, 4 %, With sodium tetrahydroborate, (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride, oxygen in ethanol, ben34 % zene, Time= 1h, Ambient temperature Takeuchi, Masayuki; Kano, Koji; Bulletin of the Chemical Society of Japan; vol. 67; nb. 6; (1994); p. 1726 - 1733 View in Reaxys

PhCH(CH3)2-Cr(CO)3 HO

Rx-ID: 7157835 View in Reaxys 87/487 Yield 37 %

Conditions & References With potassium tert-butylate, oxygen in dimethyl sulfoxide Top, Siden; Jaouen, Gerard; McGlinchey, Michael; Journal of the Chemical Society, Chemical Communications; nb. 14; (1980); p. 643 - 644 View in Reaxys

Br–+Mg

tricycloacetone peroxide HO

Rx-ID: 7157837 View in Reaxys 88/487 Yield

Conditions & References With benzene Gilman; Adams; Journal of the American Chemical Society; vol. 47; (1925); p. 2818 View in Reaxys With methoxybenzene Gilman; Adams; Journal of the American Chemical Society; vol. 47; (1925); p. 2818 View in Reaxys

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O OH

HO O

Rx-ID: 33644719 View in Reaxys 89/487 Yield

Conditions & References With perchloric acid, 4C16H36N(1+)*HO40PV2W10 (4-), dihydrogen peroxide in water, acetonitrile, tert-butyl alcohol, Time= 1h, T= 59.84 °C , p= 760.051Torr , Inert atmosphere, chemoselective reaction Kamata, Keigo; Yamaura, Taiyo; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 51; nb. 29; (2012); p. 7275 - 7278 View in Reaxys

Rx-ID: 36651243 View in Reaxys 90/487 Yield

Conditions & References

11.4 With sulfuric acid in water, Time= 12h, T= 80 °C %ChroChaudhuri, Basab; Organic Process Research and Development; vol. 3; nb. 3; (1999); p. 220 - 223 mat., 5.6 %Chromat. View in Reaxys O N

O O

N O

Rx-ID: 1709980 View in Reaxys 91/487 Yield

Conditions & References With ammonium cerium(IV) nitrate in acetonitrile, T= 30 °C , Irradiation Baciocchi, E.; Giacco, T. Del; Rol, C.; Sebastiani, G. V.; Tetrahedron Letters; vol. 26; nb. 4; (1985); p. 541 - 544 View in Reaxys O O

N O

O O

N O

Rx-ID: 1990031 View in Reaxys 92/487 Yield

C+

Rx-ID: 2261590 View in Reaxys 93/487 Yield

Conditions & References With perchloric acid, sodium perchlorate, water in various solvent(s), T= 25 °C , Rate constant, Equilibrium constant

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Amyes, Tina L.; Richard, John P.; Novak, Michael; Journal of the American Chemical Society; vol. 114; nb. 21; (1992); p. 8032 - 8041 View in Reaxys

O HO

Rx-ID: 3117017 View in Reaxys 94/487 Yield

Conditions & References With 2,6-di-tert-butyl-4-methyl-phenol in acetone, T= -13 °C , further temperatures (-33 --> -13 deg C); Arrhenius parameters (log A, E), Product distribution, Mechanism, Kinetics Pryor, William A.; Ohto, Norio; Church, Daniel F.; Journal of the American Chemical Society; vol. 105; nb. 11; (1983); p. 3614 - 3622 View in Reaxys

O Ti

(v4)

O O

Rx-ID: 3383083 View in Reaxys 95/487 Yield

Conditions & References

96 %

in diethyl ether, Time= 48h, Ambient temperature Weidmann, Beat; Seebach, Dieter; Helvetica Chimica Acta; vol. 63; nb. 8; (1980); p. 2451 - 2454 View in Reaxys O

P O

Rx-ID: 4990541 View in Reaxys 96/487 Yield 20 %, 26 %

Conditions & References in tetrahydrofuran, Time= 0.166667h, T= -78 °C Maeda, Hatsuo; Takahashi, Kenji; Ohmori, Hidenobu; Tetrahedron; vol. 54; nb. 40; (1998); p. 12233 - 12242 View in Reaxys

26 %, 20 %

in tetrahydrofuran, Time= 0.166667h, T= -78 °C Maeda, Hatsuo; Takahashi, Kenji; Ohmori, Hidenobu; Tetrahedron; vol. 54; nb. 40; (1998); p. 12233 - 12242 View in Reaxys

Rx-ID: 8811955 View in Reaxys 97/487 Yield

Conditions & References With 4-oxo-2-thioxo thiazolidine in chlorobenzene, T= 109.85 °C , Kinetics, Further Variations: Reagents Epishina; Filippenko; Shendrik; Nikolaevskii; Petroleum Chemistry; vol. 40; nb. 6; (2000); p. 426 - 431 View in Reaxys For the Phosphorus molybdenum Compounds 1 to 7, phosphorus molybdenum amine compounds 8 to 10, Comparative Products 1 and 2, and Compound 11 (zinc thiophosphate), the secondary oxidation-preventing abilities were evaluated by the following method. To a 100-ml autoclave including a glass inner cylinder tube, 37.5 g of toluene, 2.5 g of cumene hydroperoxide (hereinafter, abbreviated as CHP), and each of the above-mentioned compounds were added so that the mixture has a phosphorus content of 50 ppm by mass, followed by sealing. The autoclave was placed in a 70° C shaking constant-temperature bath, followed by shaking at 70 times/min. 4 hours later, a sample

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was taken, and the peroxide value was measured to analyze the amount of residual CHP. The amount of residual CHP is represented as a percentage with respect to the initial amount of CHP. The amount of phenol, which was produced by the action of the compound as a secondary antioxidant, was determined by gas chromatography. The amount of phenol produced by ion decomposition of the total amount of cumene hydroperoxide added first was defined as 100percent, and the results are represented as percentages with respect to the total amount. Table 1 shows the results. CHP produces phenol by ion decomposition and produces cumyl alcohol, acetophenone, or the like by radical decomposition via various radicals. Production of radicals is not preferable from the viewpoint of preventing oxidation, and hence a production of larger amount of phenol suggests that the compound has higher antioxidant ability. With C64H136Mo4O24P4, Time= 4h, T= 70 °C , Product distribution / selectivity Patent; Adeka Corporation; EP2039698; (2009); (A1) English View in Reaxys

Co(acac)2(py)(OOcumyl)

SiH

Si O

Rx-ID: 9991029 View in Reaxys 98/487 Yield

Conditions & References

37 %, 19 %, 5 %

in 1,2-dichloro-ethane, Time= 2h, T= 20 °C Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys

O transtrans trans

trans

Rx-ID: 29757147 View in Reaxys 99/487 Yield

Conditions & References Stage 1: With i-Bu2AlO3SCH3 in diethyl ether, Time= 6h, T= 25 °C , Inert atmosphere Stage 2: With hydrogenchloride, water in diethyl ether, Time= 2h, Inert atmosphere, regioselective reaction Cha, Jin Soon; Noh, Minyeong; Bulletin of the Korean Chemical Society; vol. 31; nb. 4; (2010); p. 840 - 844 View in Reaxys

Li O

Rx-ID: 1724277 View in Reaxys 100/487 Yield

Conditions & References With N,N,N',N,-tetramethylethylenediamine in hexane, Time= 18h, T= 20 °C , Yield given Ho, Tse-Lok; Synthetic Communications; vol. 13; nb. 9; (1983); p. 769 - 772 View in Reaxys

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–

Zn 2+

Rx-ID: 1981274 View in Reaxys 101/487 Yield

Conditions & References

2.9 g, 3.4 in acetic acid, Time= 2h, T= 10 - 15 °C g, 5.9 g, 72 Gurudutt, K. N.; Rao, L. Jagan Mohan; Rao, Sanjay; Srinivas, P.; Indian Journal of Chemistry, Section B: Organic % Chemistry Including Medicinal Chemistry; vol. 32; nb. 4; (1993); p. 468 - 470 View in Reaxys S

O O

S HO

racemate

Rx-ID: 2894326 View in Reaxys 102/487 Yield

Conditions & References With methyllithium in tetrahydrofuran, Time= 0.166667h, T= -50 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Kpegba, Kafui; Metzner, Patrick; Rakotonirina, Rose; Tetrahedron; vol. 45; nb. 7; (1989); p. 2041 - 2056 View in Reaxys

Rx-ID: 4983340 View in Reaxys 103/487 Yield

Conditions & References With tert.-butylhydroperoxide, tetrabutylammomium bromide, copper dichloride in dichloromethane, water, Time= 4h, T= 25 °C , Yield given. Yields of byproduct given Rothenberg, Gadi; Feldberg, Liron; Wiener, Harold; Sasson, Yoel; Journal of the Chemical Society. Perkin Transactions 2; nb. 11; (1998); p. 2429 - 2434 View in Reaxys

Rx-ID: 10161639 View in Reaxys 104/487 Yield

Conditions & References With 4-methoxy-phenol in acetonitrile, T= 25 °C , thermal decomposition, Product distribution, Further Variations: Solvents, concentrations Snelgrove; Lusztyk; Banks; Mulder; Ingold; Journal of the American Chemical Society; vol. 123; nb. 3; (2001); p. 469 - 477 View in Reaxys

O F

Rx-ID: 10245773 View in Reaxys 105/487

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Yield

Conditions & References With 2,6-dimethylpyridine, water in various solvent(s), T= 25 °C , Kinetics Creary, Xavier; Willis, Elizabeth D.; Gagnon, Madeleine; Journal of the American Chemical Society; vol. 127; nb. 51; (2005); p. 18114 - 18120 View in Reaxys

I HO

Rx-ID: 10540313 View in Reaxys 106/487 Yield

Conditions & References Stage 1: With sodium hydride in tetrahydrofuran, Time= 0.5h, T= 20 °C Stage 2: With strontium in tetrahydrofuran, Time= 0.75h, T= 20 °C Miyoshi, Norikazu; Matsuo, Tsuyoshi; Asaoka, Masashi; Matsui, Aki; Wada, Makoto; Chemistry Letters; vol. 36; nb. 1; (2007); p. 28 - 29 View in Reaxys

Rx-ID: 31323227 View in Reaxys 107/487 Yield

Conditions & References With dihydrogen peroxide in water, acetonitrile, Time= 24h, T= 80 °C Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys With dihydrogen peroxide in water, acetonitrile, Time= 24h, T= 80 °C Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys

O O

O N

N O

O N

O OH

Rx-ID: 34413862 View in Reaxys 108/487 Yield 100 %, 100 %

Conditions & References With tri-iso-propylsilane, water, trifluoroacetic acid, Time= 0.833333h, Time, Reagent/catalyst, Solvent Jamous, Mazen; Haberkorn, Uwe; Mier, Walter; Tetrahedron Letters; vol. 53; nb. 50; (2012); p. 6810 - 6814 View in Reaxys

Rx-ID: 36935610 View in Reaxys 109/487 Yield

Conditions & References With [Fe(dnbpn)(OTf)2] in acetonitrile, T= 24.84 °C

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Zhang, Qiao; Gorden, John D.; Goldsmith, Christian R.; Inorganic Chemistry; vol. 52; nb. 23; (2013); p. 13546 13554 View in Reaxys

Rx-ID: 1627775 View in Reaxys 110/487 Yield

Conditions & References

25 %, 62 %

With methyllithium, iron(III) chloride in diethyl ether, from -78 deg C up to 20 deg C, 18 h Kauffmann, Thomas; Neiteler, Christel; Neiteler, Gabriele; Chemische Berichte; vol. 127; nb. 4; (1994); p. 659 666 View in Reaxys O

Rx-ID: 2017826 View in Reaxys 111/487 Yield

Conditions & References With 5,10,15,20-tetrakisphenylporphyrinatoiron(III) chloride in methanol, dichloromethane, T= 30 °C , oxygen transfer to (TPP)Fe(III)(Cl) with/without buffer, Rate constant Lee, William A.; Yuan, Lung-Chi; Bruice, Thomas C.; Journal of the American Chemical Society; vol. 110; nb. 13; (1988); p. 4277 - 4283 View in Reaxys

(v3)

Fe – 4

3 Cl –

Li+

O Cl

Rx-ID: 2707408 View in Reaxys 112/487 Yield

Conditions & References

4 %, 55 %

in tetrahydrofuran, Time= 18h, -70 deg C to r.t. Kauffmann, Thomas; Laarmann, Barbara; Menges, Detlef; Voss, Karl-Uwe; Wingbermuehle, Dorothea; Tetrahedron Letters; vol. 31; nb. 4; (1990); p. 507 - 510 View in Reaxys

55 %, 4 %

N NH 2

Rx-ID: 3591664 View in Reaxys 113/487 Yield

Conditions & References in diethyl ether, water Lee, Soon W.; Miller, Glenn A.; Campana, Charles F.; Maciejewski, Mary L.; Trogler, William C.; Journal of the American Chemical Society; vol. 109; nb. 16; (1987); p. 5050 - 5051 View in Reaxys

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O HO

Rx-ID: 4980891 View in Reaxys 114/487 Yield

Conditions & References With tetrabutylammomium bromide, copper dichloride in dichloromethane, water, Time= 4h, T= 25 °C , Yield given. Yields of byproduct given Rothenberg, Gadi; Feldberg, Liron; Wiener, Harold; Sasson, Yoel; Journal of the Chemical Society. Perkin Transactions 2; nb. 11; (1998); p. 2429 - 2434 View in Reaxys

Rx-ID: 5048191 View in Reaxys 115/487 Yield 51 % Chromat., 46 % Chromat., 3 % Chromat.

Conditions & References With Amberlite IRA-400, borohydride form, copper(II) sulfate in methanol, Time= 3h, T= 20 °C , Reduction Sim, Tae Bo; Yoon, Nung Min; Bulletin of the Chemical Society of Japan; vol. 70; nb. 5; (1997); p. 1101 - 1107 View in Reaxys

I I

Rx-ID: 5053124 View in Reaxys 116/487 Yield

Conditions & References With (tBuOOCO)2, Time= 2h, Heating, deiodination Dolenc, Darko; Plesnicar, Bozo; Journal of the American Chemical Society; vol. 119; nb. 11; (1997); p. 2628 2632 View in Reaxys I I 2H

Rx-ID: 5053129 View in Reaxys 117/487 Yield

O HO

ring product O

Rx-ID: 6731165 View in Reaxys 118/487 Yield

Conditions & References With oxygen, ozone in acetone, Time= 24h, T= -75 °C , Irradiation, further periods of time, Product distribution Pryor, William A.; Ohto, Norio; Church, Daniel F.; Journal of the American Chemical Society; vol. 105; nb. 11; (1983); p. 3614 - 3622

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View in Reaxys

Rx-ID: 9005084 View in Reaxys 119/487 Yield

Conditions & References With tetraethylammonium chloride in isopropyl alcohol, Time= 29h, T= 90 °C Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys

SiH

Co(acac)2(py)(OOcumyl)

O Si

Rx-ID: 9991027 View in Reaxys 120/487 Yield

Conditions & References

60 %, 33 %

in 1,2-dichloro-ethane, Time= 2h Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys

O O

compound C18H16O6(?)

n-heptanols, n-heptanones HO

Rx-ID: 18177435 View in Reaxys 121/487 Yield

Conditions & References Reaction Steps: 2 1: 3 percent / MeI, Ce powder, I2 / tetrahydrofuran / 3 h / -20 °C 2: 1) Ce powder, I2 / !) THF, -20 deg C, 2) THF, -20 deg C, 3 h With cerium, iodine, methyl iodide in tetrahydrofuran Fukuzawa, Shin-ichi; Fujinami, Tatsuo; Sakai, Shizuyoshi; Journal of Organometallic Chemistry; vol. 299; (1986); p. 179 - 186 View in Reaxys Reaction Steps: 2 1: 3 percent / Ce powder, I2 / tetrahydrofuran / 3 h / -20 °C 2: 1) Ce powder, I2 / !) THF, -20 deg C, 2) THF, -20 deg C, 3 h With cerium, iodine in tetrahydrofuran Fukuzawa, Shin-ichi; Fujinami, Tatsuo; Sakai, Shizuyoshi; Journal of Organometallic Chemistry; vol. 299; (1986); p. 179 - 186 View in Reaxys

2-ferrocenylmethylidene-1,3-diphenylpropane-1,3-dione HO

Rx-ID: 26039600 View in Reaxys 122/487 Yield 22 %

Conditions & References in diethyl ether, benzene, Time= 3h, T= 20 °C

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Klimova; Berestneva, T. Klimova; Mendoza, J. M. Martinez; Stivalet, J. M. Mendez; Toscano; Garcia, M. Martinez; Synthetic Communications; vol. 38; nb. 14; (2008); p. 2299 - 2315 View in Reaxys HO

Rx-ID: 28764093 View in Reaxys 123/487 Yield

Conditions & References

81 %Chromat., 10.5 %Chromat., 8.5 %Chromat.

With cytochrome P450BM3 CYP102A1 monooxygenase, NADPH, bovine liver catalase in dimethyl sulfoxide, T= 30 °C , pH= 7.4, aq. buffer, Enzymatic reaction Whitehouse, Christopher J.C.; Bell, Stephen G.; Wong, Luet-Lok; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 10905 - 10908 View in Reaxys

Rx-ID: 40650413 View in Reaxys 124/487 Yield

Conditions & References

42 %Chromat.

With hydrogenchloride, tetrabutyl-ammonium chloride, sodium chloride in water, T= 20 °C , UV-irradiation, Green chemistry Liu, Shouxin; Zhang, Qi; Li, Huiying; Yang, Yihua; Tian, Xia; Whiting, Andrew; Chemistry - A European Journal; vol. 21; nb. 27; (2015); p. 9671 - 9675 View in Reaxys

O N

O O

Rx-ID: 2017887 View in Reaxys 125/487 Yield

Conditions & References With dinitrogen tetraoxide, nitrogen(IV) oxide in hexane, T= -10.1 °C , various solvents, effect of base, Kinetics, Product distribution, Mechanism Pryor, William A.; Castle, Laurence; Church, Daniel F.; Journal of the American Chemical Society; vol. 107; nb. 1; (1985); p. 211 - 217 View in Reaxys O O

(v3)

Co –

Li+ O

Rx-ID: 2017994 View in Reaxys 126/487 Yield 51 %, 9 %

Conditions & References in diethyl ether, Time= 18h, -78 deg C to r.t. Kauffmann, Thomas; Hopp, Gudrun; Laarmann, Barbara; Stegemann, Dieter; Wingbermuehle, Dorothea; Tetrahedron Letters; vol. 31; nb. 4; (1990); p. 511 - 514 View in Reaxys

9 %, 51 %

in diethyl ether, Time= 18h, -78 deg C to r.t. Kauffmann, Thomas; Hopp, Gudrun; Laarmann, Barbara; Stegemann, Dieter; Wingbermuehle, Dorothea; Tetrahedron Letters; vol. 31; nb. 4; (1990); p. 511 - 514 View in Reaxys

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Rx-ID: 2077327 View in Reaxys 127/487 Yield

Conditions & References in 2,2,4-trimethylpentane, T= 140 - 160 °C , Thermodynamic data, Rate constant Nudel'man, Z. N.; Myshkovskii, V. I.; Antonovskii, V. L.; J. Appl. Chem. USSR (Engl. Transl.); vol. 62; nb. 1.2; (1989); p. 139 - 143,126 - 130 View in Reaxys With pentaerythritol tetraallyl ether in 2,2,4-trimethylpentane, Time= 5h, T= 145 °C , various temperatures, various solvents, Product distribution, Rate constant Chodak, Ivan; Bakos, Dusan; Zimanyova, Edita; Collection of Czechoslovak Chemical Communications; vol. 46; nb. 2; (1981); p. 484 - 489 View in Reaxys T= 125.85 °C , homolysis, Kinetics, Further Variations: Pressures, Solvents Zhulin; Lipovich; Antonovskii; Russian Journal of Physical Chemistry A; vol. 73; nb. 6; (1999); p. 883 - 888 View in Reaxys in acetonitrile, Time= 29h, T= 90 °C , Kinetics, Product distribution, Further Variations: Solvents, Catalysts Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys With tetraethylammonium bromide in isopropyl alcohol, Time= 29h, T= 90 °C Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys With neopentyl butanoate, T= 144.84 - 164.84 °C , Decomposition, Kinetics, Product distribution, Further Variations: Reagents, Temperatures Smith, John R. Lindsay; Nagatomi, Eiji; Stead, Angela; Waddington, David J.; Beviere, Stephane D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 6; (2000); p. 1193 1198 View in Reaxys

O HO

Rx-ID: 3117018 View in Reaxys 128/487 Yield

Conditions & References With 2,6-di-tert-butyl-4-methyl-phenol in acetone, T= -18 °C , Arrhenius parameters; other temperatures, reagents ratio, Rate constant, Thermodynamic data, Mechanism Pryor, William A.; Ohto, Norio; Church, Daniel F.; Journal of the American Chemical Society; vol. 104; nb. 21; (1982); p. 5813 - 5814 View in Reaxys

Rx-ID: 3831646 View in Reaxys 129/487

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Yield

Conditions & References With hydrogen, oxygen, T= 37 °C , p= 720Torr , Irradiation, variation of quantity of O2; effect of Me3N and pyridine, Product distribution Fornarini; Speranza; Attina; Cacace; Giacomello; Journal of the American Chemical Society; vol. 106; nb. 9; (1984); p. 2498 - 2501 View in Reaxys

Rx-ID: 3917178 View in Reaxys 130/487 Yield

O O

Rx-ID: 4151653 View in Reaxys 131/487 Yield

Conditions & References

8 % Chromat., 1 % Chromat., 91 % Chromat.

With oxygen, dimethyldioxiran in acetone, Time= 22h, p= 760Torr , Ambient temperature

62 %Chromat., 2 %Chromat., 12 %Chromat.

With C30H44F6MnN6O6S2, hydrogen peroxide in acetic acid, acetonitrile, Time= 4h, T= 0 °C , Catalytic behavior, Re-

Bravo, Anna; Fontana, Francesca; Fronza, Giovanni; Mele, Andrea; Minisci, Francesco; Journal of the Chemical Society, Chemical Communications; nb. 15; (1995); p. 1573 - 1574 View in Reaxys

agent/catalyst Ottenbacher, Roman V.; Talsi, Evgenii P.; Bryliakov, Konstantin P.; ACS Catalysis; vol. 5; nb. 1; (2015); p. 39 44 View in Reaxys

O– N+

Cl OO

Rx-ID: 4511324 View in Reaxys 132/487 Yield

Conditions & References

46 % Spectr., 92 % Spectr.

With perchloric acid in acetonitrile, T= 24.9 °C , Irradiation, Rate constant, Quantum yield Fujita, Morifumi; Ishida, Akito; Takamuku, Setsuo; Fukuzumi, Shunichi; Journal of the American Chemical Society; vol. 118; nb. 36; (1996); p. 8566 - 8574 View in Reaxys

I HO

Rx-ID: 5082428 View in Reaxys 133/487

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Yield

Conditions & References With dibenzoyl peroxide, Time= 24h, Heating, deiodination Dolenc, Darko; Plesnicar, Bozo; Journal of the American Chemical Society; vol. 119; nb. 11; (1997); p. 2628 2632 View in Reaxys

ring product O

Rx-ID: 6731166 View in Reaxys 134/487 Yield

Conditions & References With oxygen, ozone in acetone, Time= 4h, T= -40 °C , further periods of time, Product distribution Pryor, William A.; Ohto, Norio; Church, Daniel F.; Journal of the American Chemical Society; vol. 105; nb. 11; (1983); p. 3614 - 3622 View in Reaxys O

O O

Me4(PrO)4(μ-PrO)2W2 HO

Rx-ID: 7044158 View in Reaxys 135/487 Yield 20 %, 56 %

Conditions & References in tetrahydrofuran, -78 deg C to 66 deg C in 1 h; 66 deg C, 3 h Kauffmann, Thomas; Jordan, Jan; Voss, Karl-Uwe; Wilde, Heinz-Wilhelm; Chemische Berichte; vol. 126; nb. 9; (1993); p. 2083 - 2092 View in Reaxys

56 %, 20 %

in tetrahydrofuran, -78 deg C to 66 deg C in 1 h; 66 deg C, 3 h Kauffmann, Thomas; Jordan, Jan; Voss, Karl-Uwe; Wilde, Heinz-Wilhelm; Chemische Berichte; vol. 126; nb. 9; (1993); p. 2083 - 2092 View in Reaxys

Rx-ID: 31323226 View in Reaxys 136/487 Yield

Rx-ID: 2017893 View in Reaxys 137/487 Yield 43.41 %, 25.83 %,

Conditions & References With magnesium 2-ethylhexanoate in chlorobenzene, Time= 6h, T= 130 °C , Kinetics Nurullina; Batyrshin; Kharlampidi, Kh. E.; Petroleum Chemistry; vol. 54; nb. 1; (2014); p. 65 - 68; Neftekhimiya; vol. 54; nb. 1; (2014); p. 66 - 69,4

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10.2 %, 5.53 %

View in Reaxys With bis(O,O'-diethyl dithiophosphato)nickel(II), T= 109.9 °C , investigation of decomposition promoted by different metal DDPs, Thermodynamic data, Product distribution, Mechanism Sexton, Michael D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 11; (1984); p. 1771 - 1776 View in Reaxys With dihydrogen peroxide in water, acetonitrile, Time= 24h, T= 80 °C Estrada, Ana C.; Simoes, Mario M. Q.; Santos, Isabel C. M. S.; Neves, M. Graca P. M. S.; Cavaleiro, Jose A. S.; Cavaleiro, Ana M. V.; Monatshefte fur Chemie; vol. 141; nb. 11; (2010); p. 1223 - 1235 View in Reaxys

Rx-ID: 2155406 View in Reaxys 138/487 Yield

Conditions & References

4 %, 96 %

in dimethyl sulfoxide, T= 33.5 °C Hirota, Hiroshi; Mitsuhashi, Tsutomu; Chemistry Letters; nb. 5; (1990); p. 803 - 806 View in Reaxys

96 %, 4 %

in dimethyl sulfoxide, T= 33.5 °C , Rate constant, Mechanism Hirota, Hiroshi; Mitsuhashi, Tsutomu; Chemistry Letters; nb. 5; (1990); p. 803 - 806 View in Reaxys

O HO

O O

Rx-ID: 3117019 View in Reaxys 139/487 Yield

Conditions & References in acetone, T= -20 °C , further temperatures (-33 --> -12 deg C); influence of 2,6-di-tert-butyl-4-methylphenol; Arrhenius parameters (log A, E), Product distribution, Mechanism, Kinetics Pryor, William A.; Ohto, Norio; Church, Daniel F.; Journal of the American Chemical Society; vol. 105; nb. 11; (1983); p. 3614 - 3622 View in Reaxys

81 % Spectr., 19 % Spectr.

in acetone, T= -10 °C , Kinetics, Further Variations: Solvents, Temperatures, also in the presence of 2,6-di-tert-butyl-4-methylphenol Cerkovnik, Janez; Erzen, Evgen; Koller, Joze; Plesnicar, Bozo; Journal of the American Chemical Society; vol. 124; nb. 3; (2002); p. 404 - 409 View in Reaxys OH

I O

Rx-ID: 3384191 View in Reaxys 140/487 Yield 55 %, 27 %

Conditions & References With Pr, 1.) THF, 20 deg C, 2.) -20 deg C

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Gailyunas, G. A.; Biktimirov, R. Kh.; Monakov, Yu. B.; Tolstikov, G. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 34; (1985); p. 2629; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1985); p. 2830 - 2831 View in Reaxys 27 %, 55 %

With Pr, 1.) THF, 20 deg C, 2.) -20 deg C Gailyunas, G. A.; Biktimirov, R. Kh.; Monakov, Yu. B.; Tolstikov, G. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 34; (1985); p. 2629; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1985); p. 2830 - 2831 View in Reaxys

(v1)

Rx-ID: 4033041 View in Reaxys 141/487 Yield

Conditions & References

6 %, 37 %, With sodium tetrahydroborate, (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride, oxygen in ethanol, ben14 % zene, Time= 4h, Ambient temperature Takeuchi, Masayuki; Kano, Koji; Bulletin of the Chemical Society of Japan; vol. 67; nb. 6; (1994); p. 1726 - 1733 View in Reaxys O P+

Cl – O

Rx-ID: 4996559 View in Reaxys 142/487 Yield

Conditions & References

33 % Chromat., 10 % Chromat.

in tetrahydrofuran, Time= 0.166667h, T= -22 °C

10 % Chromat., 33 % Chromat.

in tetrahydrofuran, Time= 0.166667h, T= -22 °C

Maeda, Hatsuo; Takahashi, Kenji; Ohmori, Hidenobu; Tetrahedron; vol. 54; nb. 40; (1998); p. 12233 - 12242 View in Reaxys

Rx-ID: 9055089 View in Reaxys 143/487 Yield

Conditions & References Stage 1: With magnesium in diethyl ether, Time= 2h, Heating Stage 2: in diethyl ether, Time= 8h, T= 20 °C , Further stages.

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Liang, Xifu; Bols, Mikael; Journal of the Chemical Society. Perkin Transactions 1; nb. 4; (2002); p. 503 - 508 View in Reaxys

O O

(v4)

Rx-ID: 11116696 View in Reaxys 144/487 Yield 0.28 g, 0.28 g, 0.02 g, 0.014 g

Conditions & References Stage 1: in benzene, Time= 24h, T= 20 °C Stage 2: With sulfuric acid in diethyl ether, Further stages. Further byproducts. Stepovik; Gulenova; Russian Journal of General Chemistry; vol. 76; nb. 2; (2006); p. 235 - 244 View in Reaxys

S Cl

N O

O O

S N

HO Cl

S Cl

Rx-ID: 11172809 View in Reaxys 145/487 Yield 23 %, 19 %

Conditions & References in various solvent(s), Time= 0.166667h, T= 150 °C , microwave irradiation, Further byproducts. Hartung, Jens; Schneiders, Nina; Gottwald, Thomas; Tetrahedron Letters; vol. 48; nb. 34; (2007); p. 6027 - 6030 View in Reaxys

Rx-ID: 28764094 View in Reaxys 146/487 Yield 20 %, 21 %

Conditions & References With perchloric acid, C13H30N4*Fe(3+)*CF3O3S(1-)*C2H2F3O(1-)*C6H5IO in 2,2,2-trifluoroethanol, acetone, Time= 0.166667h, T= -40 °C , Inert atmosphere, Schlenk technique, Kinetics, Reagent/catalyst Hong, Seungwoo; Wang, Bin; Seo, Mi Sook; Lee, Yong-Min; Kim, Myoung Jin; Kim, Hyung Rok; Ogura, Takashi; Garcia-Serres, Ricardo; Clemancey, Martin; Latour, Jean-Marc; Nam, Wonwoo; Angewandte Chemie - International Edition; vol. 53; nb. 25; (2014); p. 6388 - 6392; Angew. Chem.; vol. 126; nb. 25; (2014); p. 6506 - 6510,5 View in Reaxys

79 %Chro- With cytochrome P450BM3 CYP102A1 variant KSK19 (F87A/H171L/Q307H/N319Y) monooxygenase, NADPH, bovine liver mat., 19.5 catalase in dimethyl sulfoxide, T= 30 °C , pH= 7.4, aq. buffer, Enzymatic reaction %Chromat. Whitehouse, Christopher J.C.; Bell, Stephen G.; Wong, Luet-Lok; Chemistry - A European Journal; vol. 14; nb. 35; (2008); p. 10905 - 10908 View in Reaxys

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45 %Chro- With [(1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclotridecane)FeIII(OOC(O)CH3)]2+ in 2,2,2-trifluoroethanol, acetone, mat., 11 T= -60 °C , Inert atmosphere, Kinetics, Catalytic behavior, Reagent/catalyst, Time, Concentration, Temperature, che%Chromat. moselective reaction Wang, Bin; Lee, Yong-Min; Clmancey, Martin; Seo, Mi Sook; Sarangi, Ritimukta; Latour, Jean-Marc; Nam, Wonwoo; Journal of the American Chemical Society; vol. 138; nb. 7; (2016); p. 2426 - 2436 View in Reaxys O

HO HO

Rx-ID: 33176494 View in Reaxys 147/487 Yield

Conditions & References With [Fe(III)(dpaq)(H2O)](ClO4)2*H2O in acetonitrile, T= 20 °C Hitomi, Yutaka; Arakawa, Kengo; Funabiki, Takuzo; Kodera, Masahito; Angewandte Chemie - International Edition; vol. 51; nb. 14; (2012); p. 3448 - 3452 View in Reaxys

O S O

HO Si

Rx-ID: 39242797 View in Reaxys 148/487 Yield

Conditions & References Reaction Steps: 3 1: acetone / methanol / |Irradiation; |Inert atmosphere 2: lithium hydroxide hydrate / dichloromethane; water / 48 h / -10 - 20 °C 3: acetone / |Irradiation; |Inert atmosphere With acetone, lithium hydroxide hydrate in methanol, dichloromethane, water Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys Reaction Steps: 3 1: acetone / methanol / |Irradiation; |Inert atmosphere 2: sodium hydroxide / toluene / -10 - 60 °C 3: acetone / |Irradiation; |Inert atmosphere With acetone, sodium hydroxide in methanol, toluene Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys

O Si

Rx-ID: 39242856 View in Reaxys 149/487 Yield

Conditions & References Reaction Steps: 3 1: boron tribromide / dichloromethane / 3 h / -78 °C 2: lithium hydroxide hydrate / dichloromethane; water / 48 h / -10 - 20 °C 3: acetone / |Irradiation; |Inert atmosphere With boron tribromide, acetone, lithium hydroxide hydrate in dichloromethane, water

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Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys Reaction Steps: 3 1: boron tribromide / dichloromethane / 3 h / -78 °C 2: sodium hydroxide / toluene / -10 - 60 °C 3: acetone / |Irradiation; |Inert atmosphere With boron tribromide, acetone, sodium hydroxide in dichloromethane, toluene Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys OH Si HO

Rx-ID: 39242866 View in Reaxys 150/487 Yield

Conditions & References Reaction Steps: 2 1: sodium hydroxide / toluene / -10 - 60 °C 2: acetone / |Irradiation; |Inert atmosphere With acetone, sodium hydroxide in toluene Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys Reaction Steps: 2 1: lithium hydroxide hydrate / dichloromethane; water / 48 h / -10 - 20 °C 2: acetone / |Irradiation; |Inert atmosphere With acetone, lithium hydroxide hydrate in dichloromethane, water Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys

Li O

Rx-ID: 1552000 View in Reaxys 151/487 Yield 21 % Chromat., 23 % Chromat. 22 % Chromat., 71 % Chromat.

22 % Chromat., 71 % Chromat.

Conditions & References in tetrahydrofuran, Time= 0.5h, T= -78 °C , Title compound not separated from byproducts Lipshutz, Bruce H.; Kozlowski, Joseph A.; Breneman, Curt M.; Journal of the American Chemical Society; vol. 107; nb. 11; (1985); p. 3197 - 3204 View in Reaxys in tetrahydrofuran, Time= 0.5h, T= -78 °C , reaction with other lithium cuprates; reaction of other oxo compounds, Product distribution Lipshutz, Bruce H.; Kozlowski, Joseph A.; Breneman, Curt M.; Journal of the American Chemical Society; vol. 107; nb. 11; (1985); p. 3197 - 3204 View in Reaxys in tetrahydrofuran, Time= 0.5h, T= -78 °C , Title compound not separated from byproducts Lipshutz, Bruce H.; Kozlowski, Joseph A.; Breneman, Curt M.; Journal of the American Chemical Society; vol. 107; nb. 11; (1985); p. 3197 - 3204 View in Reaxys

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I O

Rx-ID: 4091445 View in Reaxys 152/487 Yield

Conditions & References With N,N,N',N',N'',N''-hexamethylphosphoric triamide, Sm(OTf)2, 1.) THF, cyclohexane, RT, 1 h, 2.) THF, cyclohexane, RT, 0.5 h, Yield given. Multistep reaction Fukuzawa, Shin-ichi; Tsuchimoto, Teruhisa; Kanai, Takeshi; Chemistry Letters; nb. 11; (1994); p. 1981 - 1984 View in Reaxys With N,N,N',N',N'',N''-hexamethylphosphoric triamide, sec.-butyllithium, Sm(OTf)3, 1.) THF, cyclohexane, room temperature, 1 h, 2.) THF, cyclohexane, room temperature, 1 h, Yield given. Multistep reaction Fukuzawa, Shin-Ichi; Mutoh, Keisuke; Tsuchimoto, Teruhisa; Hiyama, Tamejiro; Journal of Organic Chemistry; vol. 61; nb. 16; (1996); p. 5400 - 5405 View in Reaxys

O Mg Br

Rx-ID: 4684031 View in Reaxys 153/487 Yield

Conditions & References

14 % Chromat., 26 % Chromat.

in tetrahydrofuran, Time= 0.166667h, T= -22 °C Maeda, Hatsuo; Okamoto, Junko; Ohmori, Hidenobu; Tetrahedron Letters; vol. 37; nb. 30; (1996); p. 5381 - 5384 View in Reaxys

acetophenone, benzoic acid HO

Rx-ID: 7450710 View in Reaxys 154/487 Yield

Conditions & References With calcium hydroxide powder, T= 130 - 140 °C , Einleiten von Luft Patent; Monsanto Chem. Co.; US2447400; (1946) View in Reaxys O O

O S

Rx-ID: 31007065 View in Reaxys 155/487 Yield

Conditions & References With lithium aluminium tetrahydride in diethyl ether Kawasaki, Tsuneomi; Matsumura, Yukari; Tsutsumi, Takashi; Suzuki, Kenta; Ito, Masateru; Soai, Kenso; Science; vol. 324; nb. 5926; (2009); p. 492 - 495 View in Reaxys

Rx-ID: 31007069 View in Reaxys 156/487 Yield

Conditions & References Reaction Steps: 3 1: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate / dichloromethane 2: pyridine; 4-(N,N-dimethlyamino)pyridine 3: lithium aluminium tetrahydride / diethyl ether

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With pyridine, titanium(IV) isopropylate, tert.-butylhydroperoxide, 4-(N,N-dimethlyamino)pyridine, lithium aluminium tetrahydride, D-(-)-diisopropyl tartrate in diethyl ether, dichloromethane Kawasaki, Tsuneomi; Matsumura, Yukari; Tsutsumi, Takashi; Suzuki, Kenta; Ito, Masateru; Soai, Kenso; Science; vol. 324; nb. 5926; (2009); p. 492 - 495 View in Reaxys HO

Rx-ID: 31007080 View in Reaxys 157/487 Yield

Conditions & References Reaction Steps: 2 1: pyridine; 4-(N,N-dimethlyamino)pyridine 2: lithium aluminium tetrahydride / diethyl ether With pyridine, 4-(N,N-dimethlyamino)pyridine, lithium aluminium tetrahydride in diethyl ether Kawasaki, Tsuneomi; Matsumura, Yukari; Tsutsumi, Takashi; Suzuki, Kenta; Ito, Masateru; Soai, Kenso; Science; vol. 324; nb. 5926; (2009); p. 492 - 495 View in Reaxys

Rx-ID: 31066174 View in Reaxys 158/487 Yield

Conditions & References Reaction Steps: 3 1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 1 h / Reflux 2: pyridine / 2 h / Cooling with ice 3: water; N,N-dimethyl-aniline / acetonitrile / 25 °C With pyridine, hydroxylamine hydrochloride, water, N,N-dimethyl-aniline, sodium hydroxide in ethanol, water, acetonitrile, 3: Beckmann reaction Yamamoto, Yutaro; Hasegawa, Hiroto; Yamataka, Hiroshi; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4652 - 4660 View in Reaxys

N HO

Rx-ID: 31066226 View in Reaxys 159/487 Yield

Conditions & References Reaction Steps: 2 1: pyridine / 2 h / Cooling with ice 2: water; N,N-dimethyl-aniline / acetonitrile / 25 °C With pyridine, water, N,N-dimethyl-aniline in acetonitrile, 2: Beckmann reaction Yamamoto, Yutaro; Hasegawa, Hiroto; Yamataka, Hiroshi; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4652 - 4660 View in Reaxys

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O S

HO Si

Rx-ID: 39242779 View in Reaxys 160/487 Yield

Conditions & References Reaction Steps: 3 1: methanol / |Irradiation; |Inert atmosphere 2: lithium hydroxide hydrate / dichloromethane; water / 3.17 h / -10 - 20 °C 3: acetone / |Irradiation; |Inert atmosphere With acetone, lithium hydroxide hydrate in methanol, dichloromethane, water Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys

Rx-ID: 39242792 View in Reaxys 161/487 Yield

Conditions & References Reaction Steps: 3 1: acetone / methanol / |Irradiation; |Inert atmosphere 2: lithium hydroxide hydrate / dichloromethane; water / 3.17 h / -10 - 20 °C 3: acetone / |Irradiation; |Inert atmosphere With acetone, lithium hydroxide hydrate in methanol, dichloromethane, water Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys

F F

S O

O O HO

Rx-ID: 39242819 View in Reaxys 162/487 Yield

Conditions & References Reaction Steps: 3 1: methanol / |Irradiation; |Inert atmosphere 2: sodium hydroxide / toluene / -10 - 60 °C 3: acetone / |Irradiation; |Inert atmosphere With acetone, sodium hydroxide in methanol, toluene Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys

O Si

Rx-ID: 39242831 View in Reaxys 163/487

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Yield

Conditions & References Reaction Steps: 3 1: boron tribromide / dichloromethane / 3 h / -78 °C 2: lithium hydroxide hydrate / dichloromethane; water / 3.17 h / -10 - 20 °C 3: acetone / |Irradiation; |Inert atmosphere With boron tribromide, acetone, lithium hydroxide hydrate in dichloromethane, water Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys O O

Rx-ID: 39242842 View in Reaxys 164/487 Yield

O P O

O HO

Rx-ID: 39242846 View in Reaxys 165/487 Yield

Conditions & References Reaction Steps: 3 1: methanol / |Irradiation; |Inert atmosphere 2: lithium hydroxide hydrate / dichloromethane; water / 48 h / -10 - 20 °C 3: acetone / |Irradiation; |Inert atmosphere With acetone, lithium hydroxide hydrate in methanol, dichloromethane, water Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys

Rx-ID: 39242851 View in Reaxys 166/487 Yield

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Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys

Si OH

Rx-ID: 39242860 View in Reaxys 167/487 Yield

Conditions & References Reaction Steps: 2 1: lithium hydroxide hydrate / dichloromethane; water / 3.17 h / -10 - 20 °C 2: acetone / |Irradiation; |Inert atmosphere With acetone, lithium hydroxide hydrate in dichloromethane, water Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys O N

Rx-ID: 2019491 View in Reaxys 168/487 Yield

Conditions & References

26 %, 15 %

Time= 2h, T= -78 °C Collins, Scott; Hong, Yaping; Tetrahedron Letters; vol. 28; nb. 38; (1987); p. 4391 - 4394 View in Reaxys O

Rx-ID: 2071312 View in Reaxys 169/487 Yield

Conditions & References With lanthanum trifluoromethanesulphonate, 1.) Et2O, -78 deg C then up to 0 deg C, 2.) -78 up to 25 deg C, 30 min, Yield given. Multistep reaction. Yields of byproduct given Collins, Scott; Hong, Yaping; Hoover, Gordon J.; Veit, Jennifer R.; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3565 - 3568 View in Reaxys With lithium bromide, lanthanum trifluoromethanesulphonate, ether, -78 deg C, 30 min, Yield given. Multistep reaction Collins, Scott; Hong, Yaping; Tetrahedron Letters; vol. 28; nb. 38; (1987); p. 4391 - 4394 View in Reaxys

N E N

O O

Rx-ID: 3198421 View in Reaxys 170/487 Yield

Conditions & References With oxygen, egg phosphatidylcholine in 1,2-dichloro-benzene, T= 30 °C , p= 760Torr , add of inhibitor α-tocopherol; in bilayers dispersion; var. solv.: isooctane, nujol; var. reag.:α-dilinoleoylphosphatidylcholine, α- dimyristoylphosphatidylcholine, and α-dipalmitoylphosphatidylcholine, Product distribution, Rate constant

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Coates Barclay; Kong; VanKessel; Canadian Journal of Chemistry; vol. 64; nb. 11; (1986); p. 2103 - 2108 View in Reaxys

O Cl Ca

Rx-ID: 3527035 View in Reaxys 171/487 Yield

Conditions & References

70.1 %

Time= 1h, Ambient temperature Mochida, K.; Ogawa, H.; Journal of Organometallic Chemistry; vol. 243; nb. 2; (1983); p. 131 - 136 View in Reaxys

Rx-ID: 3774646 View in Reaxys 172/487 Yield

Conditions & References With oxygen, bis(acetylacetonate)oxovanadium in chlorobenzene, T= 49.9 °C , Rate constant Howard, J. A.; Tait, J. C.; Yamada, T.; Chenier, H. B.; Canadian Journal of Chemistry; vol. 59; (1981); p. 2184 2190 View in Reaxys

Me4(PrO)4(μ-PrO)2W2

Rx-ID: 6712334 View in Reaxys 173/487 Yield 22 %, 25 %, 26 %

Conditions & References in tetrahydrofuran Kauffmann, Thomas; Jordan, Jan; Voss, Karl-Uwe; Wilde, Heinz-Wilhelm; Chemische Berichte; vol. 126; nb. 9; (1993); p. 2083 - 2092 View in Reaxys

25 %, 26 %, 22 %

in tetrahydrofuran Kauffmann, Thomas; Jordan, Jan; Voss, Karl-Uwe; Wilde, Heinz-Wilhelm; Chemische Berichte; vol. 126; nb. 9; (1993); p. 2083 - 2092 View in Reaxys

22 %, 26 %, 25 %

in tetrahydrofuran Kauffmann, Thomas; Jordan, Jan; Voss, Karl-Uwe; Wilde, Heinz-Wilhelm; Chemische Berichte; vol. 126; nb. 9; (1993); p. 2083 - 2092 View in Reaxys

(-)(S)-2-phenyl-propylamine

H HO

Rx-ID: 7624773 View in Reaxys 174/487 Yield

Conditions & References With sulfuric acid, sodium nitrite

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Levene; Marker; Journal of Biological Chemistry; vol. 103; (1933); p. 373,376, 380 View in Reaxys

O O

Rx-ID: 9004230 View in Reaxys 175/487 Yield

Conditions & References in acetonitrile, Time= 60h, T= 90 °C Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys O

O S O

Rx-ID: 10294864 View in Reaxys 176/487 Yield

Conditions & References With oxygen, [NMQ][BF4] in acetonitrile, Photolysis, Further byproducts given Baciocchi, Enrico; Del Giacco, Tiziana; Giombolini, Paolo; Lanzalunga, Osvaldo; Tetrahedron; vol. 62; nb. 27; (2006); p. 6566 - 6573 View in Reaxys

N N

Rx-ID: 11015761 View in Reaxys 177/487 Yield

Conditions & References in acetonitrile, Flash photolysis Galli, Carlo; Gentili, Patrizia; Lanzalunga, Osvaldo; Lucarini, Marco; Pedulli, Gian Franco; Chemical Communications; nb. 20; (2004); p. 2356 - 2357 View in Reaxys

Rx-ID: 11141807 View in Reaxys 178/487 Yield

Conditions & References With air, cyclohexene, carbon, Time= 24h, Heating Sereda, Grigoriy; Rajpara, Vikul; Tetrahedron Letters; vol. 48; nb. 19; (2007); p. 3417 - 3421 View in Reaxys O

Rx-ID: 11174840 View in Reaxys 179/487

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Yield

Conditions & References With dihydrogen peroxide, polymer-anchored [VO(fsal-ea)*DMF] in acetonitrile, T= 80 °C , Product distribution, Further Variations: Temperatures, Catalysts, catalyst amount Maurya, Mannar R.; Kumar, Umesh; Manikandan; European Journal of Inorganic Chemistry; nb. 16; (2007); p. 2303 - 2314 View in Reaxys O N

Rx-ID: 17624189 View in Reaxys 180/487 Yield

Conditions & References Reaction Steps: 2 1: 1.) samarium(III) trifluoromethanesulfonate, s-butyllithium, hexamethylphosphoric triamide / 1.) THF, cyclohexane, room temperature, 1 h, 2.) THF, cyclohexane, room temperature, 1 h 2: 1.) samarium(III) trifluoromethanesulfonate, s-butyllithium, hexamethylphosphoric triamide / 1.) THF, cyclohexane, room temperature, 1 h, 2.) THF, cyclohexane, room temperature, 1 h With N,N,N',N',N'',N''-hexamethylphosphoric triamide, sec.-butyllithium, Sm(OTf)3 Fukuzawa, Shin-Ichi; Mutoh, Keisuke; Tsuchimoto, Teruhisa; Hiyama, Tamejiro; Journal of Organic Chemistry; vol. 61; nb. 16; (1996); p. 5400 - 5405 View in Reaxys

S O

Rx-ID: 28168626 View in Reaxys 181/487 Yield

Conditions & References

5 %Chromat., 40 %Chromat., 18 %Chromat., 2 %Chromat., 18 %Chromat.

With 2,4,6-triphenylpyrylium-tetrafluoroborate in acetonitrile, Irradiation, Inert atmosphere Bonesi, Sergio M.; Fagnoni, Maurizio; Albini, Angelo; European Journal of Organic Chemistry; nb. 15; (2008); p. 2612 - 2620 View in Reaxys

methylmagnesium halogenide O

Rx-ID: 33488035 View in Reaxys 182/487 Yield 80 %

Conditions & References Stage 1:Grignard reaction Stage 2:Acidic conditions, Grignard reaction Taha, Ahmed A.; International Journal of Chemical Kinetics; vol. 44; nb. 8; (2012); p. 514 - 523 View in Reaxys

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Si O

Rx-ID: 34466051 View in Reaxys 183/487 Yield

Conditions & References With SO3H silica gel, Time= 0.5h, T= 25 °C Fujii, Hideaki; Yamada, Takaaki; Hayashida, Kohei; Kuwada, Miki; Hamasaki, Atom; Nobuhara, Kazunori; Ozeki, Sumio; Nagase, Hiroshi; Heterocycles; vol. 85; nb. 11; (2012); p. 2685 - 2691 View in Reaxys

O O

Rx-ID: 34834263 View in Reaxys 184/487 Yield

Conditions & References With 2C4H4N2O(1-)*Cu(2+), oxygen, Time= 24h, T= 89.84 °C , p= 2250.23Torr , Temperature Luz; Leon; Boronat; Llabres I Xamena; Corma; Catalysis Science and Technology; vol. 3; nb. 2; (2013); p. 371 379 View in Reaxys

Mg Br O

Rx-ID: 40209977 View in Reaxys 185/487 Yield

Conditions & References in diethyl ether, T= 0 - 20 °C , Inert atmosphere Shao, Xinxin; Xu, Chunfa; Lu, Long; Shen, Qilong; Journal of Organic Chemistry; vol. 80; nb. 6; (2015); p. 3012 3021 View in Reaxys

Rx-ID: 1709985 View in Reaxys 186/487 Yield 92.8 %

Conditions & References With Stannous Hydroxide, oxygen, 29H,31H-Phthalocyanine, Time= 5.7h, T= 110 °C , mechanism; other times and temperatures; other phthalocyanines; various concentrations of reagent; activation energies, Kinetics, Thermodynamic data, Product distribution Kropf, Heinz; Vogel, Werner; Hopf, Christiane; Journal of Chemical Research, Miniprint; nb. 1; (1986); p. 301 314 View in Reaxys

88.8 %

With AlCl-phthalocyanine, oxygen, 29H,31H-Phthalocyanine, Time= 1.1h, T= 130 °C , mechanism; other times and temperatures; other phthalocyanine; further reagent; various concentrations of reagent; activation energies, Kinetics, Thermodynamic data, Product distribution Kropf, Heinz; Vogel, Werner; Journal of Chemical Research, Miniprint; nb. 1; (1986); p. 315 - 342 View in Reaxys

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Rx-ID: 1990032 View in Reaxys 187/487 Yield

Conditions & References With iron(II) diperchlorate, hexaoxo-.mu.-peroxodisulfate(2-), Cu(II) perchlorate in water, acetonitrile, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Camaioni, Donald M.; Franz, James A.; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1607 - 1613 View in Reaxys With iron(II) diperchlorate, hexaoxo-.mu.-peroxodisulfate(2-), copper (I) perchlorate in water, acetonitrile, Ambient temperature, other reaction conditions, competitive oxidation with bibenzyl, Mechanism, Product distribution Camaioni, Donald M.; Franz, James A.; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1607 - 1613 View in Reaxys

(v1)

Rx-ID: 1999352 View in Reaxys 188/487 Yield

Conditions & References in tetrachloromethane, T= 30 °C , other solvents, Rate constant Avila, David V.; Brown; Ingold; Lusztyk; Journal of the American Chemical Society; vol. 115; nb. 2; (1993); p. 466 - 470 View in Reaxys

O Li

Rx-ID: 2707466 View in Reaxys 189/487 Yield

Conditions & References With lanthanum trifluoromethanesulphonate, 1.) THF, -78 deg C then up to 0 deg C, 2.) -78 deg C, 30 min, Yield given. Multistep reaction Collins, Scott; Hong, Yaping; Hoover, Gordon J.; Veit, Jennifer R.; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3565 - 3568 View in Reaxys

Rx-ID: 3477046 View in Reaxys 190/487 Yield 70 %

Conditions & References With tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 3h, Ambient temperature, cleavage with Et4NF in MeCN; cleavage of acetals with tetraalkylammonium fluoride salts; protection and deprotection of alcohols with chloromethoxysilanes, Product distribution Gundersen, Lise-Lotte; Benneche, Tore; Undheim, Kjell; Acta Chemica Scandinavica; vol. 43; nb. 7; (1989); p. 706 - 709 View in Reaxys

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Rx-ID: 3477874 View in Reaxys 191/487 Yield

Conditions & References

66 %

With tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 4h, Ambient temperature, cleavage with Et4NF in MeCN; cleavage of acetals with tetraalkylammonium fluoride salts; protection and deprotection of alcohols with chloromethoxysilanes, Product distribution Gundersen, Lise-Lotte; Benneche, Tore; Undheim, Kjell; Acta Chemica Scandinavica; vol. 43; nb. 7; (1989); p. 706 - 709 View in Reaxys

Rx-ID: 3923373 View in Reaxys 192/487 Yield

Conditions & References With sodium tetrahydroborate, oxygen, cobalt-salen complex in ethylene glycol dimethyl ether, isopropyl alcohol, Time= 16h, Ambient temperature, other catalysts, Mechanism, Product distribution Okamoto, Tadashi; Oka, Shinzaburo; Journal of Organic Chemistry; vol. 49; nb. 9; (1984); p. 1589 - 1594 View in Reaxys

(v1)

Rx-ID: 4148978 View in Reaxys 193/487 Yield

Conditions & References in tetrachloromethane, T= 24.9 °C , var. solvents, Rate constant Avila, David V.; Ingold; Lusztyk; Green; Procopio; Journal of the American Chemical Society; vol. 117; nb. 10; (1995); p. 2929 - 2930 View in Reaxys

(v1)

O HO

(v1)

Rx-ID: 4209475 View in Reaxys 194/487 Yield

Conditions & References in tetrachloromethane, T= 24.9 °C , var. solvents; equilibrium constants for hydrogen bond formation between reagent and solvent, Rate constant Avila, David V.; Ingold; Lusztyk; Green; Procopio; Journal of the American Chemical Society; vol. 117; nb. 10; (1995); p. 2929 - 2930 View in Reaxys

O HO

Rx-ID: 4615884 View in Reaxys 195/487 Yield

Conditions & References With water in acetonitrile, T= 60 °C , kinetic data for solvolysis reactions Thibblin, Alf; Saeki, Yoshihiro; Journal of Organic Chemistry; vol. 62; nb. 4; (1997); p. 1079 - 1082 View in Reaxys

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N+

O– Cl O OO

Rx-ID: 4634103 View in Reaxys 196/487 Yield

Conditions & References With water in acetonitrile, T= 60 °C , kinetic deuterium isotope effect; further temperatures and solvents, Rate constant, Mechanism Thibblin, Alf; Saeki, Yoshihiro; Journal of Organic Chemistry; vol. 62; nb. 4; (1997); p. 1079 - 1082 View in Reaxys N O– Cl O OO

N+

Rx-ID: 4654564 View in Reaxys 197/487 Yield

Conditions & References With water in acetonitrile, T= 60 °C , kinetic deuterium isotope effect; further temperatures, Rate constant Thibblin, Alf; Saeki, Yoshihiro; Journal of Organic Chemistry; vol. 62; nb. 4; (1997); p. 1079 - 1082 View in Reaxys N

O– N+ 2H

2H 2H

Cl OO

Rx-ID: 4655231 View in Reaxys 198/487 Yield

Conditions & References With water in acetonitrile, T= 60 °C , further temperatures and solvents, Rate constant Thibblin, Alf; Saeki, Yoshihiro; Journal of Organic Chemistry; vol. 62; nb. 4; (1997); p. 1079 - 1082 View in Reaxys O O

Me4CoLi2

Rx-ID: 7446252 View in Reaxys 199/487 Yield

Conditions & References

9 %, 79 %

SiH

Co(acac)2(py)(OOcumyl)

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O HO

Rx-ID: 9991028 View in Reaxys 200/487 Yield 15 %, 38 %, 18 %

Conditions & References in 1,2-dichloro-ethane, Time= 2h Wu, Jin-Ming; Kunikawa, Shigeki; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; Kim, HyeSook; Wataya, Yusuke; Tetrahedron; vol. 61; nb. 42; (2005); p. 9961 - 9968 View in Reaxys O

Rx-ID: 1980168 View in Reaxys 201/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide, Time= 20h, T= 120 °C , Yield given. Further byproducts given. Yields of byproduct given Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386 View in Reaxys O

E HO

Rx-ID: 1986237 View in Reaxys 202/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide, Time= 12h, T= 137 °C , Yield given. Further byproducts given. Yields of byproduct given Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386 View in Reaxys

HO HO

Rx-ID: 2012178 View in Reaxys 203/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide, Time= 10h, T= 120 °C , Yield given. Further byproducts given. Yields of byproduct given Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386 View in Reaxys

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Rx-ID: 2015426 View in Reaxys 204/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide, Time= 15h, T= 120 °C , Yield given. Further byproducts given. Yields of byproduct given Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386 View in Reaxys

Rx-ID: 2017889 View in Reaxys 205/487 Yield

Conditions & References With [Fe(phthalocyanine)] in various solvent(s), T= 20 °C , use of cobalt phthalocyanine, effects of added N-(2naphthyl)aniline and various solvents, 40 deg C, Rate constant, Product distribution Kropf, Heinz; Spangenberg, Jochen; Gunst, Andreas; Hinrichsen, Jens; Liebigs Annalen der Chemie; nb. 12; (1980); p. 1923 - 1938 View in Reaxys

3.80 mmol, With cobalt naphthenate in benzene, T= 25 °C , variation of initial CHP concentrations, Rate constant, Product dis0.17 mmol, tribution, Mechanism 1.20 mmol Sawada, Hideo; Ishigaki, Hideyo; Kato, Mitsukuni; Nakayama, Masaharu; Bulletin of the Chemical Society of Japan; vol. 64; nb. 3; (1991); p. 785 - 788 View in Reaxys

Rx-ID: 2063662 View in Reaxys 206/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide, Time= 15h, T= 130 °C , Yield given. Further byproducts given. Yields of byproduct given Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386 View in Reaxys

K I HO

S HO

P O

Rx-ID: 2130586 View in Reaxys 207/487 Yield 34 %

Conditions & References Time= 5.5h, Irradiation, Yield given Creary, Xavier; Mehrsheikh-Mohammadi, M. E.; Journal of Organic Chemistry; vol. 51; nb. 1; (1986); p. 7 - 15 View in Reaxys

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34 %

Time= 5.5h, Irradiation, Yields of byproduct given Creary, Xavier; Mehrsheikh-Mohammadi, M. E.; Journal of Organic Chemistry; vol. 51; nb. 1; (1986); p. 7 - 15 View in Reaxys

N O

O HN

N N

N N N

Rx-ID: 3219264 View in Reaxys 208/487 Yield

Conditions & References in acetonitrile, Time= 3h, T= 60 °C , decomposition, other solvent, Rate constant Mitsuhashi Tsutomu; Journal of the American Chemical Society; vol. 108; nb. 9; (1986); p. 2394 - 2400 View in Reaxys

F Ca

Rx-ID: 3527910 View in Reaxys 209/487 Yield

Conditions & References

53.6 %

Time= 1h, Ambient temperature Mochida, K.; Ogawa, H.; Journal of Organometallic Chemistry; vol. 243; nb. 2; (1983); p. 131 - 136 View in Reaxys

Rx-ID: 4068745 View in Reaxys 210/487 Yield

Conditions & References

0.006 mmol, 0.012 mmol, 0.022 mmol

With (tBuOOCO)2, iodosylbenzene, [Fe(5,10,15,20-tetrakis-phenyl-porphyrinato)](1+) in benzene, Time= 3h, T= 50 °C , var. of reagent, catalyst, Product distribution Baciocchi, Enrico; d'Acunzo, Francesca; Galli, Carlo; Ioele, Marcella; Journal of the Chemical Society, Chemical Communications; nb. 4; (1995); p. 429 - 430 View in Reaxys

OH O

Rx-ID: 9004231 View in Reaxys 211/487 Yield

Conditions & References in isopropyl alcohol, Time= 60h, T= 90 °C Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys

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N Z

–N

N–

–N

Z Mn3+

N Z –N

Z N

N–

Mn3+

–

(v2)

Rx-ID: 11127406 View in Reaxys 212/487 Yield

Conditions & References With tetraethylammonium chloride in dichloromethane, Time= 0.5h, Product distribution, Further Variations: Reagents Lansky, David E.; Narducci Sarjeant, Amy A.; Goldberg, David P.; Angewandte Chemie - International Edition; vol. 45; nb. 48; (2006); p. 8214 - 8217 View in Reaxys

(+-)-<4-isopropyl-benzylamino>-phenyl-acetonitrile Cl

Rx-ID: 16663060 View in Reaxys 213/487 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran / 0.33 h / -22 °C 2: 33 percent Chromat. / tetrahydrofuran / 0.17 h / -22 °C in tetrahydrofuran Maeda, Hatsuo; Takahashi, Kenji; Ohmori, Hidenobu; Tetrahedron; vol. 54; nb. 40; (1998); p. 12233 - 12242 View in Reaxys

Rx-ID: 25990088 View in Reaxys 214/487 Yield

Conditions & References With supercritical CO2, oxygen, Time= 27h, T= 52 °C , Title compound not separated from byproducts.

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Theyssen, Nils; Hou, Zhenshan; Leitner, Walter; Chemistry - A European Journal; vol. 12; nb. 12; (2006); p. 3401 - 3409 View in Reaxys

Rx-ID: 27742538 View in Reaxys 215/487 Yield

Conditions & References 1 :Example 1; According to the method described in the specification, an oxidization reaction solution (1) containing 31percent by weight of cumene hydroperoxide was obtained by oxidizing cumene with an oxygen-containing gas (air) in an oxidation step. An epoxidation reaction solution (2) containing mainly propylene oxide, cumyl alcohol, unreacted propylene, and cumene was obtained by passing the oxidization reaction solution and propylene through a reactor filled with a titanium-containing silicon oxide catalyst in an epoxidation step. The unreacted propylene (3) was separated and removed from the resulting reaction solution (2) to obtain a reaction solution (4) after recovering propylene. The reaction solution (4) after recovering propylene was used in the following Example 3 and Comparative Example 1.First, the reaction solution (4) after recovering propylene was separated into a fraction of a solution (5) containing mainly cumyl alcohol and cumene and a fraction containing mainly propylene oxide in a propylene oxide purification step, and then the fraction containing mainly <n="27"/>propylene oxide was distilled with a plurality of distillation columns including extraction and distillation so as to satisfy product quality to obtain a propylene oxide product. Regarding the fraction of the solution (5) containing mainly cumyl alcohol and cumene, cumyl alcohol was subjected to a dehydration reaction and a hydrogenation reaction in a hydrogenation step to obtain cumene, which was recycled to the oxidization step.Fig. 1 is a schematic flow chart described in the specification. With titanium-containing silicon dioxide, Product distribution / selectivity Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/123384; (2008); (A1) English View in Reaxys

HO N F

B–

N+

B– F

N+ F

Rx-ID: 28676307 View in Reaxys 216/487 Yield

Conditions & References With oxygen in benzene, p= 760Torr , Irradiation, Kinetics Krumova, Katerina; Oleynik, Paul; Karam, Pierre; Cosa, Gonzalo; Journal of Organic Chemistry; vol. 74; nb. 10; (2009); p. 3641 - 3651 View in Reaxys

O HO

Rx-ID: 28676311 View in Reaxys 217/487 Yield

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O N HO

O S

Rx-ID: 33222994 View in Reaxys 218/487 Yield

Conditions & References With enzyme model catalyst, T= 25 °C , pH= 7, aq. phosphate buffer, Enzymatic reaction Yu, Shuangjiang; Zhang, Wei; Zhu, Junyan; Yin, Yanzhen; Jin, Haiyan; Zhou, Lipeng; Luo, Quan; Xu, Jiayun; Liu, Junqiu; Macromolecular Bioscience; vol. 11; nb. 6; (2011); p. 821 - 827 View in Reaxys

Rx-ID: 37274926 View in Reaxys 219/487 Yield 40.28 %, 22.09 %, 18.41 %, 6.14 %

Conditions & References With magnesium 2-ethylhexanoate in benzene, Time= 10h, T= 130 °C , Kinetics Nurullina; Batyrshin; Kharlampidi, Kh. E.; Petroleum Chemistry; vol. 54; nb. 1; (2014); p. 65 - 68; Neftekhimiya; vol. 54; nb. 1; (2014); p. 66 - 69,4 View in Reaxys F

F F

Rx-ID: 39242808 View in Reaxys 220/487 Yield 42 %, 25 %, 8 %

Conditions & References With acetone, Irradiation, Inert atmosphere Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys

O HO

O P O

Rx-ID: 39242847 View in Reaxys 221/487 Yield 30 %, 28 %

Rx-ID: 39276909 View in Reaxys 222/487 Yield

Conditions & References

36 %Chro- With [Ce[Co(η5-C5H5){P(O)(OEt)2}3]2(MnO4)2] in neat (no solvent), Time= 2h, T= 23 °C , Inert atmosphere mat., 35 %Chromat.

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Yi, Xiao-Yi; Wang, Guo-Cang; Ip, Ho-Fai; Wong, Wai-Yeung; Chen, Lizhuang; Sung, Herman H.-Y.; Williams, Ian D.; Leung, Wa-Hung; European Journal of Inorganic Chemistry; vol. 2014; nb. 35; (2014); p. 6097 - 6103 View in Reaxys 69 %Chro- With [Ce[Co(η5-C5H5){P(O)(OEt)2}3]2(NO3)2] in neat (no solvent), T= 100 °C , Catalytic behavior, Temperature, mat., 12 Reagent/catalyst %Chromat. Yi, Xiao-Yi; Wang, Guo-Cang; Ip, Ho-Fai; Wong, Wai-Yeung; Chen, Lizhuang; Sung, Herman H.-Y.; Williams, Ian D.; Leung, Wa-Hung; European Journal of Inorganic Chemistry; vol. 2014; nb. 35; (2014); p. 6097 - 6103 View in Reaxys

Rx-ID: 107977 View in Reaxys 223/487 Yield

Conditions & References With potassium phosphate, anschliessendes Erwaermen mit MnO2 Patent; Allied Chem. Corp.; US2881220; (1956) View in Reaxys With sodium hydroxide Patent; Hercules Powder Co.; US2713599; (1951) View in Reaxys

HO H 2N

Rx-ID: 1969543 View in Reaxys 224/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide, C-40 bovine liver catalase, Time= 0.0833333h, T= 25 °C , 0.1 M NaH2PO4-Na2HPO4 ( pH = 7.4 ), Rate constant, Product distribution Sayo, Hiroteru; Hosokawa, Mikio; Chemical & Pharmaceutical Bulletin; vol. 33; nb. 10; (1985); p. 4471 - 4477 View in Reaxys

O HO

Rx-ID: 2017896 View in Reaxys 225/487 Yield 51 % Chromat., 3 % Chromat., 39 % Chromat., 3 % Chromat.

Conditions & References With 2-(NHC6H13)-1,3,2-benzodioxaphospholen in chlorobenzene, T= 30 °C , other CHP-conc., further temp., further reag., Mechanism, Product distribution, Rate constant Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys With 1-(1,3,2-benzodioxaphospholan-2-yl)pyrolidine in chlorobenzene, T= -0.1 °C , other temp. (30 deg C), Rate constant Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys With 2-N(C6H11,C6H11)-1,3,2-benzodioxaphosphol in chlorobenzene, T= 0 °C , other temp. (30 deg C), Rate constant

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Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys With Brenzcatechyl-phosphorigsaureester-N-ethylanilid in chlorobenzene, T= 0 °C , other temp. (30 deg C), Rate constant Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys With Brenzcatechylphosphorigsaureester-anilid in chlorobenzene, T= 30 °C , Rate constant Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys With 2-N(C6H5,C6H5)-1,3,2-benzodioxaphosphol in chlorobenzene, T= 30 °C , Rate constant Rueger, C.; Arnold, D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 706 716 View in Reaxys

H 2N HO

Rx-ID: 3377095 View in Reaxys 226/487 Yield

Rx-ID: 3949364 View in Reaxys 227/487 Yield

Conditions & References With VO(O2)(picolinato)(H2O)2 in acetonitrile, T= 20 °C , Product distribution, Mechanism Bonchio, Marcella; Conte, Valeria; Di Furia, Fulvio; Modena, Giorgio; Moro, Stefano; Journal of Organic Chemistry; vol. 59; nb. 21; (1994); p. 6262 - 6267 View in Reaxys

Rx-ID: 4768615 View in Reaxys 228/487 Yield

Conditions & References With iron powder in pyridine, T= 25 °C , Product distribution, Kinetics Barton, Derek H. R.; Launay, Franck; Tetrahedron; vol. 53; nb. 43; (1997); p. 14565 - 14578 View in Reaxys

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O O

Rx-ID: 4770230 View in Reaxys 229/487 Yield

Conditions & References With [iron(II)(H2O)6](perchlorate)2, methylbutan-2-ol in pyridine, T= 25 °C , Product distribution, Kinetics Barton, Derek H. R.; Launay, Franck; Tetrahedron; vol. 53; nb. 43; (1997); p. 14565 - 14578 View in Reaxys

O O

Rx-ID: 4772083 View in Reaxys 230/487 Yield

O O

Rx-ID: 5006981 View in Reaxys 231/487 Yield

Conditions & References With 4,4'-di-tert-butylbiphenyl, lithium, 1.) THF, RT, 1.5 h; 2.) THF, -40 deg C to 0 deg C, Yield given. Multistep reaction Bachki, Abderrazak; Foubelo, Francisco; Yus, Miguel; Tetrahedron Letters; vol. 39; nb. 42; (1998); p. 7759 7762 View in Reaxys

sodium-<1-methyl-1-phenyl-ethyl peroxide> HO

Rx-ID: 7157836 View in Reaxys 232/487 Yield

Conditions & References With sodium hydrogensulfite Armstrong et al.; Journal of the Chemical Society; (1950); p. 666,670 View in Reaxys OH O

O HO

Rx-ID: 9017615 View in Reaxys 233/487 Yield

Conditions & References With tetraethylammonium bromide, Time= 60h, T= 90 °C , Further byproducts given Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys

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OH O

O O

Rx-ID: 9017618 View in Reaxys 234/487 Yield

Conditions & References With tetraethylammonium bromide, Time= 29h, T= 90 °C Maksyuta; Suprun; Opeida; Turovskii; Russian Journal of Organic Chemistry; vol. 37; nb. 6; (2001); p. 814 - 818 View in Reaxys

(v4)

O O O

Rx-ID: 11116697 View in Reaxys 235/487 Yield

Conditions & References

0.12 g, 0.056 g, 0.27 g, 0.008 g

in benzene, T= 20 °C , Further byproducts. Stepovik; Gulenova; Russian Journal of General Chemistry; vol. 76; nb. 2; (2006); p. 235 - 244 View in Reaxys

2H 2H

SiH

2H 2H

N O

Rx-ID: 40294558 View in Reaxys 236/487 Yield

Conditions & References

81 %Spectr.

With copper(I) oxide, 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical in benzene, Time= 22h, T= 110 °C , Sealed tube, Mechanism Zhang, Lizhi; Liu, Dong; Liu, Zhong-Quan; Organic Letters; vol. 17; nb. 10; (2015); p. 2534 - 2537 View in Reaxys

I HO

Rx-ID: 844479 View in Reaxys 237/487 Yield

Conditions & References With calcium magnesium, diethyl ether, anschliessendes Behandeln mit Benzoylchlorid Patent; Soc. Electrochim. Ugine; US2242516; (1939) View in Reaxys

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Rx-ID: 1986271 View in Reaxys 238/487 Yield

Rx-ID: 2017837 View in Reaxys 239/487 Yield 99 %, 98 %

Conditions & References in pyridine, Time= 0.166667h, Ambient temperature, dependence from educt ratio, addition of AcOH, Product distribution Barton; Csuhai; Ozbalik; Tetrahedron Letters; vol. 31; nb. 20; (1990); p. 2717 - 2820 View in Reaxys

Rx-ID: 2017880 View in Reaxys 240/487 Yield

Conditions & References With aminophenazone, catalase, T= 25 °C , determination of transient free radical by ESR; buffer (pH 7.4): 0.1 M NaH2PO4-Na2HPO4; further reag., Product distribution, Mechanism Sayo; Hosokawa; Chemical and Pharmaceutical Bulletin; vol. 28; nb. 7; (1980); p. 2077 - 2082 View in Reaxys

K+ –O

Rx-ID: 3606362 View in Reaxys 241/487 Yield

Conditions & References With benzonitrile in benzene, T= 0 - 50 °C , ΔH(act.), ΔS(act.), ΔG(act.), various nitriles, Rate constant, Kinetics, Thermodynamic data Morozov, O. S.; Mel'kin, V. I.; Vyshinskii, N. N.; Sokolov, N. A.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb. 6; (1983); p. 1380 - 1385,1240 - 1244 View in Reaxys

Rx-ID: 3747080 View in Reaxys 242/487 Yield

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Rx-ID: 3799342 View in Reaxys 243/487 Yield

I O

Rx-ID: 3990756 View in Reaxys 244/487 Yield

Conditions & References With cerium, iodine, !) THF, -20 deg C, 2) THF, -20 deg C, 3 h, Yield given. Multistep reaction. Yields of byproduct given Fukuzawa, Shin-ichi; Fujinami, Tatsuo; Sakai, Shizuyoshi; Journal of Organometallic Chemistry; vol. 299; (1986); p. 179 - 186 View in Reaxys

HO O

Rx-ID: 4770229 View in Reaxys 245/487 Yield

(v3)

Rx-ID: 31442775 View in Reaxys 246/487 Yield

Conditions & References T= 35 - 150 °C , Vacuo Haiss, Peter; Kuhn, Annette; Kuhn, Norbert; Maichle-Moessmer, Caecilia; Laufer, Stefan; Steimann, Manfred; Zeller, Klaus-Peter; European Journal of Inorganic Chemistry; nb. 22; (2011); p. 3284 - 3287 View in Reaxys

N–

(v3)

2 Li+ Cu –

(v2)

Rx-ID: 32042726 View in Reaxys 247/487 Yield

Conditions & References Inert atmosphere Genna, Douglas T.; Posner, Gary H.; Organic Letters; vol. 13; nb. 19; (2011); p. 5358 - 5361

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View in Reaxys F F

O HO

Rx-ID: 39242815 View in Reaxys 248/487 Yield

Conditions & References

21 %, 15 %, 51 %

With acetone, Irradiation, Inert atmosphere Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys

F F

Rx-ID: 39242821 View in Reaxys 249/487 Yield

Conditions & References

10 %, 15 %

O O

O P

O O

Rx-ID: 39242838 View in Reaxys 250/487 Yield

Conditions & References

21 %, 37 %, 6 %

O O

Rx-ID: 1982389 View in Reaxys 251/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide in chlorobenzene, T= 30 °C , Kinetics, Mechanism Rueger, C.; Koenig, T.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 326; nb. 4; (1984); p. 622 632 View in Reaxys

89/148

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O P

P O

Rx-ID: 2128542 View in Reaxys 252/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide in chlorobenzene, T= 30 °C , EA = 77 kJ/mol, ΔS(excit) = -42 J/ Kmol, Kinetics, Mechanism, Thermodynamic data Rueger, C.; Koenig, T.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 326; nb. 4; (1984); p. 622 632 View in Reaxys

Rx-ID: 2297352 View in Reaxys 253/487 Yield

Conditions & References With oxygen, Irradiation Maslak, Przemyslaw; Chapman, Jr. William H.; Journal of the Chemical Society, Chemical Communications; nb. 23; (1989); p. 1809 - 1811 View in Reaxys

Rx-ID: 2943011 View in Reaxys 254/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide, C-40 bovine liver catalase, T= 25 °C , 0.1 M NaH2PO4-Na2HPO4 ( pH = 7.4 ); var. time, and subst. conc., Rate constant, Mechanism, Equilibrium constant Sayo, Hiroteru; Hosokawa, Mikio; Chemical & Pharmaceutical Bulletin; vol. 33; nb. 10; (1985); p. 4471 - 4477 View in Reaxys O O

O O

Rx-ID: 2996975 View in Reaxys 255/487 Yield

O P O

O O

Rx-ID: 3095700 View in Reaxys 256/487

90/148

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Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide in chlorobenzene, T= 30 °C , EA = 54 kJ/mol, ΔS(excit) = -105 J/ Kmol, Kinetics, Mechanism, Thermodynamic data Rueger, C.; Koenig, T.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 326; nb. 4; (1984); p. 622 632 View in Reaxys

O P

Rx-ID: 3099445 View in Reaxys 257/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide in chlorobenzene, T= 30 °C , EA = 67 kJ/mol, ΔS(excit) = -65 J/ Kmol, Kinetics, Mechanism, Thermodynamic data Rueger, C.; Koenig, T.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 326; nb. 4; (1984); p. 622 632 View in Reaxys

O P

Rx-ID: 3100206 View in Reaxys 258/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide in chlorobenzene, T= 30 °C , EA = 77 kJ/mol, ΔS(excit) = -30 J/ Kmol, Kinetics, Mechanism, Thermodynamic data Rueger, C.; Koenig, T.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 326; nb. 4; (1984); p. 622 632 View in Reaxys

Li O

Rx-ID: 3383139 View in Reaxys 259/487 Yield

Conditions & References With [MoCl5] in tetrahydrofuran, diethyl ether, T= -70 °C , effect of use of var. solvents; effect of use of var. velocity of allowance, Product distribution Kauffmann, Thomas; Kieper, Gudrun; Angewandte Chemie; vol. 96; nb. 7; (1984); p. 502 - 503 View in Reaxys With [MoCl5], 1) THF, ether, -70 degC, Yield given. Multistep reaction. Yields of byproduct given Kauffmann, Thomas; Kieper, Gudrun; Angewandte Chemie; vol. 96; nb. 7; (1984); p. 502 - 503 View in Reaxys

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Rx-ID: 3528264 View in Reaxys 260/487 Yield

Conditions & References With calcium, 1) 900 deg C, 0.005 Torr, 2) 1 h, r.t., 0.005 Torr, Yield given. Multistep reaction. Yields of byproduct given Mochida, Kunio; Takeuchi, Hidenori; Hiraga, Yoo; Ogawa, Hiroyasu; Chemistry Letters; (1984); p. 1989 - 1992 View in Reaxys

Rx-ID: 3981921 View in Reaxys 261/487 Yield

Conditions & References

6 % Turnov., 4 % Turnov., 3 % Turnov.

With K5CoIIIW12O40, potassium acetate in water, T= 40 °C , var. reag: PhIO, H2O2 or enzymatic oxidations: other products; biomimetic oxidation, Product distribution, Mechanism Baciocchi, Enrico; Lanzalunga, Osvaldo; Marconi, Francesco; Tetrahedron Letters; vol. 35; nb. 52; (1994); p. 9771 - 9774 View in Reaxys

Rx-ID: 4251941 View in Reaxys 262/487 Yield

Conditions & References With cyclohexene, molybdenum diselenide, T= 50 °C , kinetics of molybdenium selenide catalyzed cumene hydroperoxide decomposition and epoxidation of olefins (cyclohexene, styrene) at 50 and 70 deg C; homolytic and heterolytic processes; effect of CuSe Smirnova, A. L.; Filippova, T. V.; Blyumberg, E. A.; Russian Chemical Bulletin; vol. 43; nb. 12; (1994); p. 2011 2014; Izvestiya Akademi Nauk, Seriya Khimicheskaya; nb. 12; (1994); p. 2130 - 2133 View in Reaxys

cocaine

OH OH

Rx-ID: 5474888 View in Reaxys 263/487 Yield

Conditions & References With diethyl ether Fraenkel; Gruber; Justus Liebigs Annalen der Chemie; vol. 433; (1923); p. 242 View in Reaxys

N E N

chlorotoluene HO

Rx-ID: 8449871 View in Reaxys 264/487 Yield

Conditions & References With bis(acetylacetonate)oxovanadium in chlorobenzene, Time= 96h, T= 29.9 °C , Product distribution

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Howard, J. A.; Tait, J. C.; Yamada, T.; Chenier, H. B.; Canadian Journal of Chemistry; vol. 59; (1981); p. 2184 2190 View in Reaxys

O–

Rx-ID: 8678860 View in Reaxys 265/487 Yield

Conditions & References With sodium t-butanolate in N,N,N',N',N'',N''-hexamethylphosphoric triamide, T= 69.85 °C , Kinetics, Further Variations: Reagents Lyavinets; Russian Journal of General Chemistry; vol. 70; nb. 4; (2000); p. 563 - 567 View in Reaxys

O O

Rx-ID: 31066161 View in Reaxys 266/487 Yield

Conditions & References With water, N,N-dimethyl-aniline in acetonitrile, T= 25 °C , Beckmann reaction, Kinetics Yamamoto, Yutaro; Hasegawa, Hiroto; Yamataka, Hiroshi; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4652 - 4660 View in Reaxys

Rx-ID: 33488044 View in Reaxys 267/487 Yield

Conditions & References With water in acetone, T= 24.84 °C , Solvolysis, Kinetics Taha, Ahmed A.; International Journal of Chemical Kinetics; vol. 44; nb. 8; (2012); p. 514 - 523 View in Reaxys

HN 5.6

NH O

Rx-ID: 35803436 View in Reaxys 268/487 Yield

Conditions & References With oxygen, UV-irradiation Geer, Michael F.; Walla, Michael D.; Solntsev, Kyril M.; Strassert, Cristian A.; Shimizu, Linda S.; Journal of Organic Chemistry; vol. 78; nb. 11; (2013); p. 5568 - 5578 View in Reaxys

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Rx-ID: 276832 View in Reaxys 269/487 Yield

Conditions & References With cobalt (II) stearate Treibs; Pellmann; Chemische Berichte; vol. 87; (1954); p. 1201,1204 View in Reaxys

Rx-ID: 278540 View in Reaxys 270/487 Yield

Conditions & References With cobalt (II) stearate Treibs; Pellmann; Chemische Berichte; vol. 87; (1954); p. 1201,1204 View in Reaxys

Rx-ID: 747163 View in Reaxys 271/487 Yield

Conditions & References With cobalt (II) stearate Treibs; Pellmann; Chemische Berichte; vol. 87; (1954); p. 1201,1204 View in Reaxys

Rx-ID: 1709975 View in Reaxys 272/487 Yield 8 % Chromat., 15 % Chromat., 8 % Chromat.

Conditions & References With air, Ptlt;NPhNC(S)SCH3gt;2 in acetonitrile, Ambient temperature, Irradiation, relative rate, Product distribution Monaci, Anna; Gazzetta Chimica Italiana; vol. 116; nb. 6; (1986); p. 339 - 340 View in Reaxys

Rx-ID: 1709984 View in Reaxys 273/487

94/148

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Yield

Conditions & References With oxygen, 1.5E-4 zinc naphthenate, Time= 3h, T= 110 °C , activation energy; different catalyst, catalyst concentrations, reaction times and temperatures, Product distribution, Kinetics, Thermodynamic data Kozlov; Tovstokhat'ko; Potekhin; Journal of applied chemistry of the USSR; vol. 59; nb. 1 pt 2; (1986); p. 122 127 View in Reaxys With oxygen, 1,10-phenanthroline, zinc naphthenate, Time= 8h, T= 100 °C , rate constants between 100-130 deg C, Kinetics, Product distribution Kozlov; Tovstokhat'ko; Potekhin; Journal of applied chemistry of the USSR; vol. 59; nb. 6 pt 2; (1986); p. 1284 1286 View in Reaxys

Rx-ID: 2017886 View in Reaxys 274/487 Yield

Conditions & References With cobalt(II) 2,4-pentanedionate in various solvent(s), T= 60 °C , with crown ethers; rate of decomposition Kochinashvili, M. V.; Kuramshin, E. M.; Kotlyar, S. A.; Zlot-skii, S. S.; Rakhmankulov, D. L.; J. Appl. Chem. USSR (Engl. Transl.); vol. 62; nb. 7.2; (1989); p. 1681 - 1684,1562 - 1564 View in Reaxys

O HO

Rx-ID: 2017891 View in Reaxys 275/487 Yield 68.03 % Chromat., 4.78 % Chromat.

Conditions & References With zinc bislt;OO-di-(p-tolyl)phosphorodithioategt; in decane, Time= 6h, T= 109.9 °C , Other promoters (e.g. zinc bis-<OO-dialkyl(aryl)phosphonodithioates, hexakis-<OO-dialkyl(aryl)phosphorodithioate>-μ4-tetraoxo-zincs, OOOOtetra-alkyl(aryl) thioperoxydiphosphates) were used; Ε(excit.), ΔH(excit.), ΔS(excit.)., Kinetics, Mechanism, Thermodynamic data Bridgewater, Alan J.; Dever, J. Robert; Sexton, Michael D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1980); p. 1006 - 1016 View in Reaxys With zinc dithiocarbamates or zinc xanthates in decane, T= 109.9 °C , E (excit.); ΔH (excit.); ΔS (excit.), Product distribution, Thermodynamic data Sexton, Michael D.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1985); p. 59 - 64 View in Reaxys

O HO

Rx-ID: 2017898 View in Reaxys 276/487 Yield

Conditions & References With tin(IV) chloride in ethyl acetate, T= 89.9 °C , E(A); lg A; other temperatures; also with InCl3, AlCl3 and Me2SnCl2; other peroxides, Kinetics, Thermodynamic data, Product distribution Aleksandrov, Yu. A.; Lelekov, V. E.; Makin, G. I.; J. Gen. Chem. USSR (Engl. Transl.); vol. 59; nb. 2.2; (1989); p. 368 - 371,322 - 325 View in Reaxys

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OH O

O P

Rx-ID: 2045174 View in Reaxys 277/487 Yield

O O

P O

O P

Rx-ID: 2053029 View in Reaxys 278/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide in chlorobenzene, T= 30 °C , EA = 67 kJ/mol, ΔS(excit) = -60 J/ Kmol, Kinetics, Mechanism, Thermodynamic data Rueger, C.; Koenig, T.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 326; nb. 4; (1984); p. 622 632 View in Reaxys

O P

O HO

Rx-ID: 2080126 View in Reaxys 279/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide in chlorobenzene, T= 30 °C , EA = 72 kJ/mol, ΔS(excit) = -62 J/ Kmol, Kinetics, Mechanism, Thermodynamic data Rueger, C.; Koenig, T.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 326; nb. 4; (1984); p. 622 632 View in Reaxys

O Si

Si O

Rx-ID: 2107874 View in Reaxys 280/487 Yield

Conditions & References With tri-N-butyl phosphate in various solvent(s), T= 179.9 °C , E(activ.), other phosphates added, Rate constant, Thermodynamic data Gorbatov, V. V.; Yablokova, N. V.; Aleksandrov, Yu. A.; Ivanov, V. I.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb. 8; (1983); p. 1752 - 1755,1576 - 1578 View in Reaxys

96/148

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O O

Rx-ID: 2835615 View in Reaxys 281/487 Yield

Conditions & References

69 %, 12 %

in various solvent(s), Time= 1h, T= 125 °C , effects of other solvents, temperature, reaction time; ΔG(excit.), ΔH(excit.), ΔS(excit.), E(excit.), Product distribution, Rate constant, Thermodynamic data Villenave, J. J.; Filliatre, C.; Maillard, B.; Jaouhari, R.; Bulletin des Societes Chimiques Belges; vol. 91; nb. 4; (1982); p. 301 - 310 View in Reaxys

O HO

Rx-ID: 4154537 View in Reaxys 282/487 Yield

Conditions & References With vanadium pentoxide in chlorobenzene, T= 69.9 °C , in the presence or absence of polystyrene, Rate constant Lyavinets, A. S.; Choban, A. F.; Chervinskii, K. A.; Russian Journal of Physical Chemistry; vol. 69; nb. 5; (1995); p. 725 - 729; Zhurnal Fizicheskoi Khimii; vol. 69; nb. 5; (1995); p. 802 - 806 View in Reaxys

N N

N O

Rx-ID: 4516211 View in Reaxys 283/487 Yield

Conditions & References With nitrogen(IV) oxide, ozone in dichloromethane, Time= 0.0166667h, T= 0 °C , var. arene/NO2 ratios, temp., reaction times, and nitrating agents, Product distribution Suzuki, Hitomi; Mori, Tadashi; Chemistry Letters; nb. 8; (1996); p. 647 - 648 View in Reaxys With oxygen, nitrogen(IV) oxide, ozone in dichloromethane, Time= 0.0833333h, T= -20 °C , further bicumene derivatives; various solvents, nitration reagents, Product distribution, Mechanism Suzuki, Hitomi; Mori, Tadashi; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); nb. 7; (1997); p. 1265 - 1274 View in Reaxys

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S O

Rx-ID: 4676584 View in Reaxys 284/487 Yield

Conditions & References With 9,10-anthracenedicarbonitrile, oxygen in acetonitrile-D3, Time= 0.666667h, T= 40 °C , Irradiation, photoinduced oxidation of benzyl phenyl sulfides promoted by 9,10-dicyanoanthracene; electron transfer reactions; reaction pathways for sulfide radical cation formed; C-S and C-H bond cleavage, S-oxidation; stability of photoproducts, Product distribution Baciocchi, Enrico; Crescenzi, Cristina; Lanzalunga, Osvaldo; Tetrahedron; vol. 53; nb. 12; (1997); p. 4469 4478 View in Reaxys

α-Methylstyrene dimers (VII) and complex phenols (VIII) O

Rx-ID: 7446260 View in Reaxys 285/487 Yield

Conditions & References

0.52 %, 0.55 %, 0.22 %

With sulfuric acid in water, T= 20 °C , Product distribution, Mechanism Zakoshanskii, V. M.; J. Gen. Chem. USSR (Engl. Transl.); vol. 59; nb. 5.2; (1989); p. 1122 - 1126,991 - 994 View in Reaxys O

O C O

(v1)

Rx-ID: 9385933 View in Reaxys 286/487 Yield

Conditions & References in benzene, Time= 12h, T= 30 °C , Kinetics Font-Sanchis, Enrique; Aliaga, Carolina; Cornejo, Raecca; Scaiano; Organic Letters; vol. 5; nb. 9; (2003); p. 1515 - 1518 View in Reaxys O

O C O

(v1)

F F

Rx-ID: 9386076 View in Reaxys 287/487 Yield

98/148

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O C

(v1)

Rx-ID: 9393151 View in Reaxys 288/487 Yield

O C

(v1)

Rx-ID: 9393152 View in Reaxys 289/487 Yield

O C

(v1)

N O

Rx-ID: 9394252 View in Reaxys 290/487 Yield

O HO

O OH

Rx-ID: 38018906 View in Reaxys 291/487 Yield

Conditions & References With C28H42O4Te in aq. phosphate buffer, ethanol, T= 25 °C , pH= 7, Kinetics, Catalytic behavior, Solvent, Reagent/ catalyst Yin; Wei; Shi; Hu; Jiao; Chen; Asian Journal of Chemistry; vol. 26; nb. 8; (2014); p. 2311 - 2314 View in Reaxys

99/148

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O S O

Rx-ID: 39242783 View in Reaxys 292/487 Yield

Conditions & References

23 %, 8 %, With acetone, Irradiation, Inert atmosphere 8 %, 8 % Crespi, Stefano; Ravelli, Davide; Protti, Stefano; Albini, Angelo; Fagnoni, Maurizio; Chemistry - A European Journal; vol. 20; nb. 52; (2014); p. 17572 - 17578 View in Reaxys O

O N O

O S

Rx-ID: 39534704 View in Reaxys 293/487 Yield

Conditions & References With C28H42O4Te, glutathione peroxidase in aq. phosphate buffer, ethanol, T= 25 °C , pH= 7, Enzymatic reaction, Kinetics, Solvent Jiao; Yin; Hu; Shi; Gan; Liang; Huang; Zhang; Asian Journal of Chemistry; vol. 27; nb. 5; (2015); p. 1671 - 1674 View in Reaxys

O HO

Rx-ID: 1671677 View in Reaxys 294/487 Yield

Conditions & References

32 %, 71 %

in diethyl ether, Time= 3h, T= 20 °C , other reagents under various conditions, Product distribution, Mechanism Fujisaka, Tomohiro; Miura, Masahiro; Nojima, Masatomo; Kusabayashi, Shigekazu; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1989); p. 1031 - 1039 View in Reaxys O

O P

P O

OH P

O HO

OH O

Rx-ID: 1862235 View in Reaxys 295/487 Yield

O O O O

O O

100/148

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O O

N N

N O

O O

Rx-ID: 1963344 View in Reaxys 296/487 Yield

Conditions & References

2 %, 24 %, in acetonitrile, Time= 5h, Irradiation 10 %, 5 % Bardi, Luca; Fasani, Elisa; Albini, Angelo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1994); p. 545 - 550 View in Reaxys

–O

S O

K+ O

Rx-ID: 2017890 View in Reaxys 297/487 Yield

Conditions & References

2.7 mmol, 3.1 mmol, 2.2 mmol, 36.7 mmol

With sulfur dioxide, potassium n-butoxide in hexane, T= 20 °C , multistep reaction, 60 deg C, styrene, Product distribution Kharitonov, A. G.; Glukhovskoi, V. S.; J. Gen. Chem. USSR (Engl. Transl.); vol. 52; nb. 2; (1982); p. 305 309,264 - 267 View in Reaxys

O HO

Rx-ID: 2017899 View in Reaxys 298/487 Yield

Conditions & References With 2-(2,6-Di-tert-butyl-4-methylphenoxyl)-1,3,2-benzo-dioxaphosphol in chlorobenzene, T= 50 °C , with water, further temp., EA, ΔS(excit.), Rate constant, Kinetics, Mechanism Schwertlick, K.; Rueger, C.; Noack, R.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 697 705 View in Reaxys

O O

Rx-ID: 2832962 View in Reaxys 299/487 Yield

Conditions & References

95 %

in various solvent(s), other solvent, Product distribution Villenave, J. J.; Filliatre, C.; Maillard, B.; Jaouhari, R.; Bulletin des Societes Chimiques Belges; vol. 91; nb. 4; (1982); p. 301 - 310 View in Reaxys

O O O

Rx-ID: 2838946 View in Reaxys 300/487

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Yield

Conditions & References

85 %, 5 %

Rx-ID: 3384269 View in Reaxys 301/487 Yield

Conditions & References 1) 20 degC, 3 d, chloroforme/benzene, 2) 20 degC, 1 h, H2O, Yield given. Multistep reaction Dormond, A.; Aaliti, A.; Moise,, C.; Tetrahedron Letters; vol. 27; nb. 13; (1986); p. 1497 - 1498 View in Reaxys

O O

O P

P HO OH

O O

Rx-ID: 3461692 View in Reaxys 302/487 Yield

(v4)

O O

Rx-ID: 4495179 View in Reaxys 303/487 Yield

Conditions & References With isopropyl-benzene in dichloromethane, T= -30 °C , other temperatures; activation parameters A', A0, ΔS0 <*>, A1; decomposition of ozone complexes with arenes; spectrophotometric study of kinetic regularities; possible mechanism of conversion of ozone complexes, Rate constant, Thermodynamic data, Kinetics Avzyanova; Kabal'nova; Shereshovets; Russian Chemical Bulletin; vol. 45; nb. 2; (1996); p. 356 - 359 View in Reaxys

Rx-ID: 8612643 View in Reaxys 304/487 Yield

Conditions & References With Fe[5,10,15,20-tetrakis(pentafluorophenyl)porphyrin]Cl, oxygen in various solvent(s), T= 100 °C , Oxidation, Product distribution, Further Variations: reaction times Evans, Steven; Smith, John R. Lindsay; Journal of the Chemical Society. Perkin Transactions 2; nb. 7; (2000); p. 1541 - 1551 View in Reaxys

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O Al

O O

Rx-ID: 2017853 View in Reaxys 305/487 Yield 2.1 mmol, 4.5 mmol, 2.5 mmol, 35.7 mmol

Conditions & References With sulfur dioxide in hexane, T= 20 °C , multistep reaction, 40 - 60 deg C, styrene, polybutadiene, Product distribution Kharitonov, A. G.; Glukhovskoi, V. S.; J. Gen. Chem. USSR (Engl. Transl.); vol. 52; nb. 2; (1982); p. 305 309,264 - 267 View in Reaxys

Al3+ O

–

S O O

Rx-ID: 2017854 View in Reaxys 306/487 Yield 1.8 mmol, 3.1 mmol, 2.1 mmol, 37.8 mmol

Conditions & References With sulfur dioxide in hexane, T= 20 °C , multistep reaction, hexane, styrene, Product distribution Kharitonov, A. G.; Glukhovskoi, V. S.; J. Gen. Chem. USSR (Engl. Transl.); vol. 52; nb. 2; (1982); p. 305 309,264 - 267 View in Reaxys

Na +

–O

Rx-ID: 2017856 View in Reaxys 307/487 Yield

Conditions & References With 2,4,6-trinitro-chlorobenzene in toluene, T= 20 °C , study of the decomposition during oxidation of polynitroarenes, Product distribution, Mechanism Kropf, Heinz; Ball, Michael; Siegfriedt, Klaus-Hermann; Wagner, Siegfried; Journal of Chemical Research, Miniprint; nb. 11; (1981); p. 4001 - 4015 View in Reaxys

Rx-ID: 2017894 View in Reaxys 308/487 Yield 27.9 % Turnov., 14.3 % Turnov.

Conditions & References With AlCl-phthalocyanine*H2O, 29H,31H-Phthalocyanine in Petroleum ether, Time= 72h, T= 100 °C , other solvents; other phthalocyanine, Kinetics, Product distribution Kropf, Heinz; Vogel, Werner; Journal of Chemical Research, Miniprint; nb. 1; (1986); p. 315 - 342 View in Reaxys

103/148

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O P O

O P

O P HO

O P

O OH

Rx-ID: 2069341 View in Reaxys 309/487 Yield

O Si

Si HO

Si O

Rx-ID: 2107872 View in Reaxys 310/487 Yield

Conditions & References With pyridine in various solvent(s), T= 150 °C , rate constant for decomposition and activation energie, various amines, Product distribution, Rate constant, Thermodynamic data Aleksandrov, Yu. A.; Gorbatov, V. V.; Yablokova, N. V.; Doklady Chemistry; vol. 250; (1980); p. 28 - 31; Dokl. Akad. Nauk SSSR Ser. Khim.; vol. 250; nb. 3; (1980); p. 623 - 626 View in Reaxys

Rx-ID: 2701560 View in Reaxys 311/487 Yield

Conditions & References With [MoCl5], acetophenone, 1) THF, ether, -70 degC,, Yield given. Multistep reaction. Yields of byproduct given Kauffmann, Thomas; Kieper, Gudrun; Angewandte Chemie; vol. 96; nb. 7; (1984); p. 502 - 503 View in Reaxys

Rx-ID: 4151652 View in Reaxys 312/487 Yield 8 % Chromat., 92 % Chromat.

Conditions & References in acetone, Time= 1h, Ambient temperature, Further byproducts given Bravo, Anna; Fontana, Francesca; Fronza, Giovanni; Mele, Andrea; Minisci, Francesco; Journal of the Chemical Society, Chemical Communications; nb. 15; (1995); p. 1573 - 1574 View in Reaxys

104/148

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S S

Rx-ID: 27981203 View in Reaxys 313/487 Yield

Conditions & References With 3-cyano-N-methylquinolinium perchlorate in acetonitrile-D3, Photolysis, Quantum yield Baciocchi, Enrico; Del Giacco, Tiziana; Lanzalunga, Osvaldo; Mencarelli, Paolo; Procacci, Barbara; Journal of Organic Chemistry; vol. 73; nb. 15; (2008); p. 5675 - 5682 View in Reaxys HO

Rx-ID: 40222625 View in Reaxys 314/487 Yield

Conditions & References With [NiII(tris(2-(pyridin-2-yl)ethyl)amine)(OAc)]BPh4, dihydrogen peroxide, triethylamine in water, acetonitrile, Time= 24h, T= 60 °C , Catalytic behavior Morimoto, Yuma; Bunno, Shuji; Fujieda, Nobutaka; Sugimoto, Hideki; Itoh, Shinobu; Journal of the American Chemical Society; vol. 137; nb. 18; (2015); p. 5867 - 5870 View in Reaxys

Rx-ID: 107981 View in Reaxys 315/487 Yield

Conditions & References T= 128 - 158 °C , Thermolysis, Kinetics Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys T= 111 - 150 °C , Thermolysis, Kinetics Bailey; Godin; Transactions of the Faraday Society; vol. 52; (1956); p. 68,71 View in Reaxys T= 111 - 150 °C , Thermolysis, Mechanism Bailey; Godin; Transactions of the Faraday Society; vol. 52; (1956); p. 68,71 View in Reaxys T= 128 - 158 °C , Thermolysis, Mechanism Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys

O O

Rx-ID: 2702881 View in Reaxys 316/487

105/148

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Yield

Conditions & References With [MoCl5] in tetrahydrofuran, diethyl ether, T= -70 °C , effect of use of var. solvents; effect of use of var. velocity of allowance; effect of use of Ph-CO-Me, Product distribution Kauffmann, Thomas; Kieper, Gudrun; Angewandte Chemie; vol. 96; nb. 7; (1984); p. 502 - 503 View in Reaxys

N+

Rx-ID: 4153583 View in Reaxys 317/487 Yield

Conditions & References With perchloric acid, isopropyl-benzene in acetonitrile, Irradiation, Quantum yield Fujita, Morifumi; Ishida, Akito; Majima, Tetsuro; Fukuzumi, Shunichi; Takamuku, Setsuo; Chemistry Letters; nb. 2; (1995); p. 111 - 112 View in Reaxys

HO O HO

acetic acid

Rx-ID: 6725969 View in Reaxys 318/487 Yield

Conditions & References With tert.-butylhydroperoxide, Al tri-t-BuO- in benzene, Time= 84h, T= 20 °C , Mechanism, Product distribution Stepovik; Dodonov; Zaburdaeva; Russian Journal of General Chemistry; vol. 67; nb. 1; (1997); p. 111 - 115 View in Reaxys

HO O

acetic acid

Rx-ID: 7450706 View in Reaxys 319/487 Yield

Conditions & References With Al tri-t-BuO- in benzene, Time= 20h, T= 70 °C , Product distribution Stepovik; Dodonov; Zaburdaeva; Russian Journal of General Chemistry; vol. 67; nb. 1; (1997); p. 111 - 115 View in Reaxys

S HO

Rx-ID: 10294863 View in Reaxys 320/487 Yield

Conditions & References With [NMQ][BF4] in acetonitrile, UV-irradiation, Quantum yield, Further Variations: Reagents Baciocchi, Enrico; Del Giacco, Tiziana; Giombolini, Paolo; Lanzalunga, Osvaldo; Tetrahedron; vol. 62; nb. 27; (2006); p. 6566 - 6573 View in Reaxys

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Rx-ID: 31442780 View in Reaxys 321/487 Yield

Conditions & References Reaction Steps: 2 1: 12 h / 20 °C 2: 35 - 150 °C / Vacuo Haiss, Peter; Kuhn, Annette; Kuhn, Norbert; Maichle-Moessmer, Caecilia; Laufer, Stefan; Steimann, Manfred; Zeller, Klaus-Peter; European Journal of Inorganic Chemistry; nb. 22; (2011); p. 3284 - 3287 View in Reaxys O

Rx-ID: 94027 View in Reaxys 322/487 Yield

Conditions & References Matsubara; Perkin; Journal of the Chemical Society; vol. 87; (1905); p. 671 View in Reaxys

O Na +

O–

Rx-ID: 95167 View in Reaxys 323/487 Yield

Conditions & References Patent; Bayer and Co.; DE166899 View in Reaxys

Rx-ID: 177135 View in Reaxys 324/487 Yield

Conditions & References Capp; Hawkins; Journal of the Chemical Society; (1953); p. 4106 View in Reaxys O

O O

Rx-ID: 673904 View in Reaxys 325/487 Yield

Conditions & References Tissier; Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 685 View in Reaxys

I HO

Rx-ID: 757729 View in Reaxys 326/487 Yield

Conditions & References Patent; Bayer and Co.; DE166898

107/148

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View in Reaxys

H O

Rx-ID: 1990028 View in Reaxys 327/487 Yield

Conditions & References With DCN, oxygen in acetonitrile, Irradiation, Quantum yield Albini, Angelo; Spreti, Silvia; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1987); p. 1175 - 1180 View in Reaxys

O Si

Si HO

Rx-ID: 2107873 View in Reaxys 328/487 Yield

Conditions & References in anhydrous butyl ether, T= 190 °C , other temperatures; other solvents; ΔE(activ.), Product distribution, Rate constant, Thermodynamic data Gorbatov, V. V.; Yablokova, N. V.; Kheidorov, V. P.; Aleksandrov, Yu. A.; J. Gen. Chem. USSR (Engl. Transl.); vol. 50; nb. 11; (1980); p. 2482 - 2486,2005 - 2008 View in Reaxys in various solvent(s), T= 179.9 °C , E(activ.), Rate constant, Thermodynamic data Gorbatov, V. V.; Yablokova, N. V.; Aleksandrov, Yu. A.; Ivanov, V. I.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb. 8; (1983); p. 1752 - 1755,1576 - 1578 View in Reaxys

O Si

O O

Rx-ID: 2107875 View in Reaxys 329/487 Yield

Conditions & References in cyclohexene, T= 169.9 °C , rate constants of thermal decomposition (temperature, solvent and pressure dependence); Ea, ΔH(excit.), ΔS(excit.), Rate constant, Product distribution, Thermodynamic data Rudakov, O. B.; Yakovlev, I. P.; Ganyushkin, A. V.; Sosnovskaya, T. A.; Zhulin, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 7; (1987); p. 1374 - 1380; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 7; (1987); p. 1489 - 1496 View in Reaxys

Rx-ID: 2942568 View in Reaxys 330/487 Yield

Conditions & References in acetonitrile, Time= 48h, T= 100 °C , add. of paraformaldehyde, Product distribution, Mechanism Humphreys, Robert W. R.; Journal of Organic Chemistry; vol. 48; nb. 9; (1983); p. 1483 - 1487

108/148

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View in Reaxys

SiH O SiH

SiH

Si O

racemate

Rx-ID: 3578985 View in Reaxys 331/487 Yield

Conditions & References in [3.3.1]nonane, T= 160 °C , ΔE(excit.), Rate constant, Kinetics, Thermodynamic data Tomadze, A. V.; Yablokova, N. V.; Yablokov, V. A.; Razuvaev, G. A.; Journal of Organometallic Chemistry; vol. 212; nb. 1; (1981); p. 43 - 50 View in Reaxys HO

O –O

Na +

Rx-ID: 4260879 View in Reaxys 332/487 Yield

Conditions & References With sodium hydroxide, sodium hypochlorite in water, Time= 0.75h, Ambient temperature, Irradiation, other aromatic sulfonic acids; var. concentration of alkali, Product distribution, Mechanism Kimura; Ogata; Bulletin of the Chemical Society of Japan; vol. 56; nb. 2; (1983); p. 471 - 473 View in Reaxys

lithium alanate HO

Rx-ID: 5474887 View in Reaxys 333/487 Yield

Conditions & References Eliel; Freeman; Journal of the American Chemical Society; vol. 74; (1952); p. 923,925 View in Reaxys

O N

N O

N-demethylated aminopyrine

Rx-ID: 5739559 View in Reaxys 334/487 Yield

Conditions & References With catalase, T= 25 °C , 0.1 M sodium phosphate buffer (pH 7.4), free radical intermediate, Mechanism Sayo; Hosokawa; Chemical and pharmaceutical bulletin; vol. 28; nb. 2; (1980); p. 683 - 685 View in Reaxys

N O

Rx-ID: 31546476 View in Reaxys 335/487

109/148

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Yield

Conditions & References in acetonitrile, T= 25 °C , Inert atmosphere, Flash photolysis, Kinetics Salamone, Michela; Dilabio, Gino A.; Bietti, Massimo; Journal of Organic Chemistry; vol. 76; nb. 15; (2011); p. 6264 - 6270 View in Reaxys

Rx-ID: 1545452 View in Reaxys 336/487 Yield

Conditions & References With molybdenym stearate, Time= 0.333333h, T= 60 °C , other time, Product distribution Garmonov, V. I.; Nazarova, A. B.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 7; (1984); p. 1632 - 1636,1454 - 1457 View in Reaxys

O P

P O

Rx-ID: 1564151 View in Reaxys 337/487 Yield

Conditions & References in chlorobenzene, T= 29.9 °C , other temperatures, Kinetics, Mechanism Koenig, T.; Habicher, W. D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 6; (1989); p. 913 - 922 View in Reaxys

P O

O P

Rx-ID: 1862356 View in Reaxys 338/487 Yield

Conditions & References in chlorobenzene, T= 29.9 °C , Rate constant, Mechanism Koenig, T.; Habicher, W. D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 6; (1989); p. 913 - 922 View in Reaxys O

P O

O O

Rx-ID: 1862715 View in Reaxys 339/487 Yield

110/148

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O P O

Rx-ID: 1864456 View in Reaxys 340/487 Yield

S P

Rx-ID: 1869016 View in Reaxys 341/487 Yield

O O

Rx-ID: 1979796 View in Reaxys 342/487 Yield

O O

Rx-ID: 2012259 View in Reaxys 343/487 Yield

111/148

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O O

O P

Rx-ID: 2017830 View in Reaxys 344/487 Yield

O O

P O

O O

Rx-ID: 2017832 View in Reaxys 345/487 Yield

O HO

O P

Rx-ID: 2017833 View in Reaxys 346/487 Yield

O O

Rx-ID: 2017834 View in Reaxys 347/487 Yield

Conditions & References in chlorobenzene, T= 29.9 °C , Rate constant, Mechanism

112/148

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Koenig, T.; Habicher, W. D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 6; (1989); p. 913 - 922 View in Reaxys

O P

Rx-ID: 2017835 View in Reaxys 348/487 Yield

P S

O S

Rx-ID: 2017838 View in Reaxys 349/487 Yield

O P

O P O

Rx-ID: 2017840 View in Reaxys 350/487 Yield

Conditions & References in chlorobenzene, T= 25 °C , various temp, and conc.; ΔS(excit.), Rate constant Schwertlick, K.; Rueger, C.; Noack, R.; Journal fuer Praktische Chemie (Leipzig); vol. 324; nb. 5; (1982); p. 697 705 View in Reaxys

113/148

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Rx-ID: 2017843 View in Reaxys 351/487 Yield

O P

Rx-ID: 2017846 View in Reaxys 352/487 Yield

Conditions & References in chlorobenzene, T= 29.9 °C , other temperature and concentration, Kinetics, Mechanism Koenig, T.; Habicher, W. D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 6; (1989); p. 913 - 922 View in Reaxys O S

S O

Rx-ID: 2017848 View in Reaxys 353/487 Yield

O O HO

P O

Rx-ID: 2017849 View in Reaxys 354/487 Yield

114/148

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H N

Rx-ID: 2017860 View in Reaxys 355/487 Yield

Rx-ID: 2017861 View in Reaxys 356/487 Yield

O O

Rx-ID: 2017862 View in Reaxys 357/487 Yield

O O

HO O

Rx-ID: 2017864 View in Reaxys 358/487 Yield

115/148

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O O

O HO

Rx-ID: 2017865 View in Reaxys 359/487 Yield

S P

Rx-ID: 2017866 View in Reaxys 360/487 Yield

P HO

Rx-ID: 2017867 View in Reaxys 361/487 Yield

O P

O O

Rx-ID: 2017868 View in Reaxys 362/487 Yield

Conditions & References in chlorobenzene, T= 29.9 °C , other concentration CHP, Kinetics, Mechanism Koenig, T.; Habicher, W. D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 6; (1989); p. 913 - 922 View in Reaxys

116/148

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O P

Rx-ID: 2017869 View in Reaxys 363/487 Yield

O O

Rx-ID: 2017870 View in Reaxys 364/487 Yield

Conditions & References in chlorobenzene, T= 27.9 °C , other temperature, Kinetics, Mechanism Koenig, T.; Habicher, W. D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 6; (1989); p. 913 - 922 View in Reaxys

Rx-ID: 2017872 View in Reaxys 365/487 Yield

Conditions & References in chlorobenzene, T= 29.9 °C , stoichiometrically, Rate constant, Mechanism Koenig, T.; Habicher, W. D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 6; (1989); p. 913 - 922 View in Reaxys

O HO

O O

P HO

O P O

Rx-ID: 2017873 View in Reaxys 366/487 Yield

Conditions & References in chlorobenzene, T= 31.9 °C , Rate constant, Mechanism

117/148

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Koenig, T.; Habicher, W. D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 6; (1989); p. 913 - 922 View in Reaxys

O P

P O

Rx-ID: 2017874 View in Reaxys 367/487 Yield

Rx-ID: 2017875 View in Reaxys 368/487 Yield

Rx-ID: 2017892 View in Reaxys 369/487 Yield

Conditions & References

0.49 %, 0.041 %, 0.26 %, 0.54 %

With acetone, F-4SK, Time= 60h, Heating, varied CHP content in org. mixture; purified or technical CHP; experiments in the presence of H2SO4 or KU-23/10-60 cation-exchange resin (without F-4SK), Product distribution Etlis; Beshenova; Semenova; Shomina; Dreiman; Balaev; Journal of applied chemistry of the USSR; vol. 59; nb. 3 pt 2; (1986); p. 551 - 555 View in Reaxys

O O

Rx-ID: 2151118 View in Reaxys 370/487 Yield

Conditions & References in various solvent(s), Time= 96h, T= 50 °C , other temp., Product distribution, Kinetics, Rate constant

118/148

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Komai, Takeshi; Kato, Kenji; Matsuyama, Kazuo; Bulletin of the Chemical Society of Japan; vol. 61; nb. 7; (1988); p. 2641 - 2642 View in Reaxys

S O

Rx-ID: 2885482 View in Reaxys 371/487 Yield

Conditions & References With potassium hydroxide, T= 19.9 °C , other alkali, Rate constant, Mechanism Lyavinets, A. S.; Choban, A. F.; Chervinskii, K. A.; Russian Journal of Physical Chemistry; vol. 67; nb. 7; (1993); p. 1225 - 1228; Zhurnal Fizicheskoi Khimii; vol. 67; nb. 7; (1993); p. 1364 - 1368 View in Reaxys O

O HO

Rx-ID: 3014692 View in Reaxys 372/487 Yield

O SiH SiH

SiH

Si O

O O

Rx-ID: 3571049 View in Reaxys 373/487 Yield

SiH

O SiH

SiH

Si O

Si Si

Rx-ID: 3572561 View in Reaxys 374/487 Yield

119/148

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O O

O P

Rx-ID: 3874739 View in Reaxys 375/487 Yield

Cl O Cl

Rx-ID: 4476259 View in Reaxys 376/487 Yield 7% Spectr., 7 % Spectr., 41 % Spectr., 14 % Spectr., 71 % Spectr.

Conditions & References With oxygen in THF-d8 (tetrahydrofuran-d8), Ambient temperature, Irradiation, electron transfer and fragmentation reactions of photogenerated methoxybicumene radical cations; effect of oxygen; back electron transfer in triplet ion pairs; formation of charge-transfer complexes between quinones and methoxybicumenes, Quantum yield, Rate constant, Product distribution Maslak, Przemyslaw; Chapman Jr., William H.; Journal of Organic Chemistry; vol. 61; nb. 8; (1996); p. 2647 2656 View in Reaxys

Rx-ID: 5143759 View in Reaxys 377/487 Yield

Conditions & References in chlorobenzene, T= 110 °C , Rate constant Farzaliev; Allakhverdiev; Rzaeva; Petroleum Chemistry; vol. 38; nb. 2; (1998); p. 126 - 131 View in Reaxys SH O

H N

Rx-ID: 5143760 View in Reaxys 378/487 Yield

Conditions & References in chlorobenzene, T= 110 °C , Rate constant Farzaliev; Allakhverdiev; Rzaeva; Petroleum Chemistry; vol. 38; nb. 2; (1998); p. 126 - 131 View in Reaxys

120/148

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Rx-ID: 5143761 View in Reaxys 379/487 Yield

Conditions & References in chlorobenzene, T= 110 °C , Rate constant Farzaliev; Allakhverdiev; Rzaeva; Petroleum Chemistry; vol. 38; nb. 2; (1998); p. 126 - 131 View in Reaxys

N H

Rx-ID: 5143763 View in Reaxys 380/487 Yield

Conditions & References in chlorobenzene, T= 110 °C , other 1,2-aminopropanethiols, Rate constant, Mechanism Farzaliev; Allakhverdiev; Rzaeva; Petroleum Chemistry; vol. 38; nb. 2; (1998); p. 126 - 131 View in Reaxys

S SH

N H

S OH

N H

Rx-ID: 5143764 View in Reaxys 381/487 Yield

Conditions & References in chlorobenzene, T= 110 °C , Rate constant Farzaliev; Allakhverdiev; Rzaeva; Petroleum Chemistry; vol. 38; nb. 2; (1998); p. 126 - 131 View in Reaxys

–O

Li+ –O

Li+

O–

Li+

Li+ O

LiOH

O–

Rx-ID: 7455122 View in Reaxys 382/487 Yield

Conditions & References in cyclohexene, Time= 8h, T= 60 °C , Yield given. Yields of byproduct given Shekunova, V. M.; Sokolov, N. A.; Aleksandrov, Yu. A.; J. Gen. Chem. USSR (Engl. Transl.); vol. 51; nb. 2; (1981); p. 299 - 302,239 - 242 View in Reaxys in cyclohexene, Time= 8h, T= 60 °C , other solvent, other temperature, other time, Kinetics, Product distribution Shekunova, V. M.; Sokolov, N. A.; Aleksandrov, Yu. A.; J. Gen. Chem. USSR (Engl. Transl.); vol. 51; nb. 2; (1981); p. 299 - 302,239 - 242 View in Reaxys

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H N

OH O

HSO2H HO

Rx-ID: 8515790 View in Reaxys 383/487 Yield

Conditions & References in chlorobenzene, T= 110 °C , Rate constant Farzaliev; Allakhverdiev; Rzaeva; Petroleum Chemistry; vol. 38; nb. 2; (1998); p. 126 - 131 View in Reaxys

(v1)

BH2

Rx-ID: 8752688 View in Reaxys 384/487 Yield

Conditions & References in benzene, T= 25 °C , Kinetics, Further Variations: Solvents Sheeller, Brad; Ingold, Keith U.; Journal of the Chemical Society. Perkin Transactions 2; nb. 4; (2001); p. 480 - 486 View in Reaxys

O HO

Rx-ID: 31066094 View in Reaxys 385/487 Yield

Conditions & References in benzene, T= 25 °C , Flash photolysis, Inert atmosphere, Kinetics, Solvent, Concentration Salamone, Michela; Giammarioli, Ilaria; Bietti, Massimo; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4645 - 4651 View in Reaxys

Rx-ID: 31066095 View in Reaxys 386/487 Yield

CH 2

Rx-ID: 31546479 View in Reaxys 387/487 Yield

122/148

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View in Reaxys

Rx-ID: 31546482 View in Reaxys 388/487 Yield

Rx-ID: 31546484 View in Reaxys 389/487 Yield

Rx-ID: 31546485 View in Reaxys 390/487 Yield

Conditions & References in 2,2,4-trimethylpentane, T= 25 °C , Inert atmosphere, Flash photolysis, Kinetics Salamone, Michela; Dilabio, Gino A.; Bietti, Massimo; Journal of Organic Chemistry; vol. 76; nb. 15; (2011); p. 6264 - 6270 View in Reaxys

(v1)

O HO

Rx-ID: 32664689 View in Reaxys 391/487 Yield

Conditions & References in acetonitrile, T= 22 °C , UV-irradiation, Inert atmosphere, Kinetics, Concentration, Solvent Bietti, Massimo; Salamone, Michela; Dilabio, Gino A.; Jockusch, Steffen; Turro, Nicholas J.; Journal of Organic Chemistry; vol. 77; nb. 3; (2012); p. 1267 - 1272 View in Reaxys

2H 2H

(v1)

Rx-ID: 34506946 View in Reaxys 392/487 Yield

Conditions & References in acetonitrile, T= 25 °C , Kinetics

123/148

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Salamone, Michela; Dilabio, Gino A.; Bietti, Massimo; Journal of Organic Chemistry; vol. 77; nb. 23; (2012); p. 10479 - 10487 View in Reaxys

CH 2

(v1)

Rx-ID: 34506948 View in Reaxys 393/487 Yield

Conditions & References in acetonitrile, T= 25 °C , Kinetics Salamone, Michela; Dilabio, Gino A.; Bietti, Massimo; Journal of Organic Chemistry; vol. 77; nb. 23; (2012); p. 10479 - 10487 View in Reaxys

Rx-ID: 140089 View in Reaxys 394/487 Yield

Conditions & References T= 128 - 158 °C , Thermolysis, Kinetics Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys T= 128 - 158 °C , Thermolysis, Mechanism Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys

Rx-ID: 172941 View in Reaxys 395/487 Yield

Rx-ID: 213216 View in Reaxys 396/487 Yield

Conditions & References T= 128 - 158 °C , Thermolysis, Kinetics

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Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys T= 128 - 158 °C , Thermolysis, Mechanism Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys

K+ O

–O

Rx-ID: 2434782 View in Reaxys 397/487 Yield

Conditions & References in benzene, T= 50 °C , other concentration, nitrogen atmosphere, Kinetics, Rate constant Sokolov, N. A.; Mel'kin, V. I.; Gavva, V. A.; J. Gen. Chem. USSR (Engl. Transl.); vol. 54; nb. 9; (1984); p. 2124 2128,1897 - 1901 View in Reaxys

H Mg Br O

Rx-ID: 2688240 View in Reaxys 398/487 Yield

Conditions & References Reetz, Manfred T.; Harmat, Nicholas; Mahrwald, Rainer; Angewandte Chemie; vol. 104; nb. 3; (1992); p. 333 334 View in Reaxys

H O Mg

Rx-ID: 2688242 View in Reaxys 399/487 Yield

Conditions & References Reetz, Manfred T.; Harmat, Nicholas; Mahrwald, Rainer; Angewandte Chemie; vol. 104; nb. 3; (1992); p. 333 334 View in Reaxys O

Mg O

Rx-ID: 2688243 View in Reaxys 400/487 Yield

Conditions & References Reetz, Manfred T.; Harmat, Nicholas; Mahrwald, Rainer; Angewandte Chemie; vol. 104; nb. 3; (1992); p. 333 334 View in Reaxys

125/148

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H N

S HO

Rx-ID: 5143762 View in Reaxys 401/487 Yield

Conditions & References in chlorobenzene, T= 110 °C , Rate constant Farzaliev; Allakhverdiev; Rzaeva; Petroleum Chemistry; vol. 38; nb. 2; (1998); p. 126 - 131 View in Reaxys

2-tert-butylperoxy-2-phenyl-propane

Rx-ID: 6678605 View in Reaxys 402/487 Yield

Conditions & References T= 75 °C Kharasch et al.; Journal of Organic Chemistry; vol. 15; (1950); p. 775,778; Journal of Organic Chemistry; vol. 16; (1951); p. 1458,1465 View in Reaxys

Rx-ID: 8942113 View in Reaxys 403/487 Yield 0.90 mmol, 0.76 mmol, 0.16 mmol, 0.012 mmol

Conditions & References With neopentyl butanoate, T= 164.84 °C , Product distribution, Further Variations: Reagents Lindsay Smith; Nagatomi; Stead; Waddington; Journal of the Chemical Society, Perkin Transactions 2; nb. 9; (2001); p. 1527 - 1533 View in Reaxys

Rx-ID: 107980 View in Reaxys 404/487 Yield

Conditions & References T= 128 - 158 °C , Thermolysis Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys

Rx-ID: 140088 View in Reaxys 405/487 Yield

Conditions & References T= 128 - 158 °C , Thermolysis Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys

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C O

Rx-ID: 172940 View in Reaxys 406/487 Yield

Conditions & References T= 128 - 158 °C , Thermolysis Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys

Rx-ID: 2017851 View in Reaxys 407/487 Yield

Conditions & References in octane, Time= 0.00138889h, T= 10 - 50 °C , K, k(eff), E(eff), preexponential factor, W0 Σ, Thermodynamic data, Equilibrium constant, Rate constant Alyasov, V. N.; Maslennikov, V. P.; Aleksandrov, Yu. A.; Kuznetsov, I. Yu.; J. Gen. Chem. USSR (Engl. Transl.); vol. 52; nb. 5; (1982); p. 1139 - 1145,996 - 1003 View in Reaxys OH (v5)

PH O S

O HO

Rx-ID: 2017877 View in Reaxys 408/487 Yield

Conditions & References in chlorobenzene, T= 74.9 °C , Rate constant Koenig, T.; Habicher, W. D.; Schwetlick, K.; Journal fuer Praktische Chemie (Leipzig); vol. 331; nb. 6; (1989); p. 913 - 922 View in Reaxys

H H 2N

Rx-ID: 2198132 View in Reaxys 409/487 Yield

Conditions & References With sodium nitrite in perchloric acid, water, Product distribution, Mechanism Kirmse, Wolfgang; Guenther, Bernd-Rainer; Loosen, Karin; Chemische Berichte; vol. 113; nb. 6; (1980); p. 2140 - 2153 View in Reaxys

127/148

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Cl Na +

–O

HO O

Rx-ID: 3451924 View in Reaxys 410/487 Yield

Conditions & References

0.20 mmol, in dichloromethane, Time= 12h, T= 20 °C , other sodium alkyl peroxide, other halonitroaromatic compounds, also in 0.03 mmol, presence of crown ethers and NaOH, var. time, Mechanism 0.20 mmol, 0.01 mmol Baj, S.; Polish Journal of Chemistry; vol. 67; nb. 11; (1993); p. 1967 - 1972 View in Reaxys

O O

Rx-ID: 5049332 View in Reaxys 411/487 Yield

Conditions & References in acetone, T= 42 °C , Oxidation, acetoxylation; elimination, Kinetics Kazakov; Kabal'nova; Khursan; Shereshovets; Russian Chemical Bulletin; vol. 46; nb. 4; (1997); p. 663 - 671 View in Reaxys

O O Br Mg

Rx-ID: 5336059 View in Reaxys 412/487 Yield

Conditions & References in diethyl ether, Addition, Product distribution Holm, Torkil; Journal of Organic Chemistry; vol. 65; nb. 4; (2000); p. 1188 - 1192 View in Reaxys

NH 2 HO

Rx-ID: 550660 View in Reaxys 413/487 Yield

Conditions & References Capp; Hawkins; Journal of the Chemical Society; (1953); p. 4106 View in Reaxys T= 110 °C Capp; Hawkins; Journal of the Chemical Society; (1953); p. 4106 View in Reaxys

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Rx-ID: 1980169 View in Reaxys 414/487 Yield

Conditions & References With alpha,alpha-dimethylbenzyl hydroperoxide, Time= 20h, T= 120 °C , other concentrations of cumene hydroperoxide; reaction of other phenyl cycloalkanes, also with tert-butyl hydroperoxide, Product distribution Pritzkow, Wilhelm; Suprun, Vladimir Ya.; Voerckel, Volkmar; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 3; (1990); p. 381 - 386 View in Reaxys

dinitrogen pentaoxide

nitrogen monooxide

1ξ-nitro-2-phenyl-propene HO

Rx-ID: 6674863 View in Reaxys 415/487 Yield

Conditions & References p= 13239.1Torr Patent; Gen. Electric Co.; US2867669; (1954) View in Reaxys

copper oxide calcium carbonate HO

Rx-ID: 6682872 View in Reaxys 416/487 Yield

Conditions & References T= 130 - 140 °C , Einleiten von Sauerstoff Patent; I. G. Farbenind.; US1813606; (1927); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 17; p. 766 View in Reaxys Patent; I. G. Farbenind.; DE522255; (1926) View in Reaxys

aqueous Na2SO3

Rx-ID: 7157833 View in Reaxys 417/487 Yield

Conditions & References T= 60 °C Hock; Lang; Chemische Berichte; vol. 77/79; (1944); p. 257,262 View in Reaxys

other amines

Rx-ID: 7157834 View in Reaxys 418/487 Yield

Conditions & References T= 110 °C Capp; Hawkins; Journal of the Chemical Society; (1953); p. 4106 View in Reaxys

129/148

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7 mol methyl magnesium bromide

O O HO

Rx-ID: 8259654 View in Reaxys 419/487 Yield

Conditions & References Versetzen der Reaktionsloesung mit wss. Salzsaeure Fieser; Heymann; Journal of the American Chemical Society; vol. 64; (1942); p. 376,381 View in Reaxys

Rx-ID: 1709956 View in Reaxys 420/487 Yield

Conditions & References With lithium aluminium tetrahydride, meta-chloroperoxybenzoic acid, 2.) ether, 30 min, reflux; study of the regioselectivity of autoxidation by reduction of the corresponding oxidation-mixture, Mechanism, Product distribution Pritzkow, Wilhelm; Thomas, Gerda; Willecke, Lothar; Journal fuer Praktische Chemie (Leipzig); vol. 327; nb. 5; (1985); p. 847 - 851 View in Reaxys

O Si

O P

Si O

O O

Rx-ID: 1862367 View in Reaxys 421/487 Yield

Conditions & References in various solvent(s), T= 343 °C , E(activ.), Rate constant, Product distribution, Mechanism Gorbatov, V. V.; Yablokova, N. V.; Aleksandrov, Yu. A.; Ivanov, V. I.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb. 8; (1983); p. 1752 - 1755,1576 - 1578 View in Reaxys

O Si

Si HO

130/148

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P O

Si O

O O

Rx-ID: 1864525 View in Reaxys 422/487 Yield

Conditions & References in various solvent(s), T= 343 °C , E(activ.), Rate constant, Mechanism, Product distribution Gorbatov, V. V.; Yablokova, N. V.; Aleksandrov, Yu. A.; Ivanov, V. I.; J. Gen. Chem. USSR (Engl. Transl.); vol. 53; nb. 8; (1983); p. 1752 - 1755,1576 - 1578 View in Reaxys

B B O

O O OH

Rx-ID: 2017847 View in Reaxys 423/487 Yield

Conditions & References in octane, Time= 0.00138889h, T= 10 - 50 °C , K, ΔH(eq), k(eff), E(eff), preexponential factor, W0 Σ, contribution of protolysis γ, Thermodynamic data, Equilibrium constant, Rate constant Alyasov, V. N.; Maslennikov, V. P.; Aleksandrov, Yu. A.; Kuznetsov, I. Yu.; J. Gen. Chem. USSR (Engl. Transl.); vol. 52; nb. 5; (1982); p. 1139 - 1145,996 - 1003 View in Reaxys

O Si

Si HO

Si O O

Rx-ID: 3310280 View in Reaxys 424/487 Yield 40 % Chromat., 26 % Chromat., 9 % Chromat., 10 % Chromat.

Conditions & References in [3.3.1]nonane, T= 160 °C , Rate constant, Thermodynamic data Gorbatov, V. V.; Yablokova, N. V.; Aleksandrov, Yu. A.; J. Gen. Chem. USSR (Engl. Transl.); vol. 50; nb. 10; (1980); p. 2274 - 2278,1840 - 1844 View in Reaxys

CH 2

(v1)

HO O

Rx-ID: 3363026 View in Reaxys 425/487 Yield

Conditions & References T= 60 °C , Rate constant

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Rizzardo, Ezio; Serelis, Algirdas K.; Solomon, David H.; Australian Journal of Chemistry; vol. 35; nb. 10; (1982); p. 2013 - 2024 View in Reaxys

N N

H 2C

O O

Rx-ID: 3363055 View in Reaxys 426/487 Yield

Conditions & References T= 60 °C , Rate constant Rizzardo, Ezio; Serelis, Algirdas K.; Solomon, David H.; Australian Journal of Chemistry; vol. 35; nb. 10; (1982); p. 2013 - 2024 View in Reaxys

O O

methyl magnesium halide HO

Rx-ID: 5807046 View in Reaxys 427/487 Yield

Conditions & References Patent; Bayer and Co.; DE166898 View in Reaxys Patent; Bayer and Co.; DE166899 View in Reaxys bei der Einwirkung auf Natriumbenzoat Patent; Bayer and Co.; DE166898 View in Reaxys Patent; Bayer and Co.; DE166899 View in Reaxys bei der Einwirkung auf Natriumbenzoat Bayer and Co; Chem. Zentralbl.; vol. 77; nb. I; (1906); p. 720 View in Reaxys Bayer and Co; Chem. Zentralbl.; vol. 77; nb. I; (1906); p. 720 View in Reaxys

oxygen HO

Rx-ID: 6674862 View in Reaxys 428/487 Yield

Conditions & References T= 195 °C Barnett et al.; Industrial and Engineering Chemistry; vol. 41; (1949); p. 2612,2614 View in Reaxys

lead (IV)-oxide

oxygen O

Rx-ID: 6682873 View in Reaxys 429/487 Yield

Conditions & References T= 130 °C Hock; Kropf; Journal fuer Praktische Chemie (Leipzig); vol. <4> 6; (1958); p. 120,123 View in Reaxys

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lead (IV)-oxide

oxygen

aluminium oxide

Rx-ID: 6682874 View in Reaxys 430/487 Yield

Conditions & References T= 130 °C Hock; Kropf; Journal fuer Praktische Chemie (Leipzig); vol. <4> 6; (1958); p. 120,123 View in Reaxys

lead (IV)-oxide

oxygen

manganese (IV)-oxide

Rx-ID: 6682875 View in Reaxys 431/487 Yield

Conditions & References T= 130 °C Hock; Kropf; Journal fuer Praktische Chemie (Leipzig); vol. <4> 6; (1958); p. 120,123 View in Reaxys

lead (IV)-oxide

oxygen

sodium hydroxide

Rx-ID: 6682876 View in Reaxys 432/487 Yield

Conditions & References T= 130 °C Hock; Kropf; Journal fuer Praktische Chemie (Leipzig); vol. <4> 6; (1958); p. 120,123 View in Reaxys

lead (IV)-oxide

oxygen

sodium peroxide

Rx-ID: 6682877 View in Reaxys 433/487 Yield

Conditions & References T= 130 °C Hock; Kropf; Journal fuer Praktische Chemie (Leipzig); vol. <4> 6; (1958); p. 120,123 View in Reaxys

lead (IV)-oxide

oxygen

zinc oxide

Rx-ID: 6682878 View in Reaxys 434/487 Yield

Conditions & References T= 130 °C

133/148

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Hock; Kropf; Journal fuer Praktische Chemie (Leipzig); vol. <4> 6; (1958); p. 120,123 View in Reaxys

cobalt naphthenate

Rx-ID: 7446257 View in Reaxys 435/487 Yield

Conditions & References T= 35 - 100 °C , Kinetics Tinjakowa; Schurawlewa; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 1262; engl. Ausg. S. 1234 View in Reaxys T= 20 °C , sowie bei 60grad, Kinetics Dierichs; Preu; ; vol. <A>; nb. 51; (1956); p. 109,116, 117 View in Reaxys

C Cl

Rx-ID: 61030 View in Reaxys 436/487 Yield

Conditions & References T= 20 °C , Photolysis, Mechanism Norrish; Searby; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 237; (1956); p. 464,471 View in Reaxys T= 20 °C , Photolysis, Quantum yield Norrish; Searby; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 237; (1956); p. 464,471 View in Reaxys

O C

Rx-ID: 209286 View in Reaxys 437/487 Yield

134/148

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Rx-ID: 3537084 View in Reaxys 438/487 Yield

Conditions & References T= 125.9 °C , kinetic isotope effect, pressure dependence, Product distribution Zhulin, V. M.; Lipovich, T. V.; Antonovskii, V. L.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 34; (1985); p. 2630; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1985); p. 2831 View in Reaxys

H 2C

(v1)

Rx-ID: 3537091 View in Reaxys 439/487 Yield

Conditions & References p= 375030Torr , solvent and pressure dependence, ratio for hydrogen atom abstraction and β-cleavage of the cumyloxy radical, competing reaction, Product distribution, Rate constant Zhulin, V. M.; Rudakov, O. B.; Stashina, G. A.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 34; nb. 5; (1985); p. 1104 - 1107; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 5; (1985); p. 1205 - 1208 View in Reaxys

cobalt naphthenate HO

benzene-isopropyl alcohol

Rx-ID: 7446259 View in Reaxys 440/487 Yield

Conditions & References T= 60 °C , Kinetics Dierichs; Preu; ; vol. <A>; nb. 51; (1956); p. 109,116, 117 View in Reaxys

n-heptanols, n-heptanones HO

Rx-ID: 7456041 View in Reaxys 441/487 Yield

Conditions & References Time= 80h, T= 125 °C , reaction with different catalysts, different reaction times, different initial conc. of hydroperoxide, Product distribution, Mechanism Lauterbach, Gerlinde; Pritzkow, W.; Tien, Tieu Dung; Voerckel, V.; Journal fuer Praktische Chemie (Leipzig); vol. 330; nb. 6; (1988); p. 933 - 946 View in Reaxys

135/148

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OH HO

sodium nitrite

S OO

H 2N

(S)-2-phenyl-propanol-(1) HO

Rx-ID: 8286745 View in Reaxys 442/487 Yield

Conditions & References anschliessendes Erwaermen auf 60grad Levene; Marker; Journal of Biological Chemistry; vol. 103; (1933); p. 373,376, 380 View in Reaxys

O Si

Rx-ID: 2936376 View in Reaxys 443/487 Yield

Conditions & References T= 169.9 °C , pressure dependence in the range 10 - 1000 MPa, Rate constant, Product distribution Zhulin, V. M.; Stashina, G. A.; Ganyushkin, A. V.; Yablokova, N. V.; Yablokov, V. A.; Rudakov, O. B.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 32; (1983); p. 1507 1510; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 7; (1983); p. 1659 - 1661 View in Reaxys

cobalt naphthenate

Rx-ID: 7446258 View in Reaxys 444/487 Yield

Conditions & References T= 35 - 100 °C , Kinetics Tinjakowa; Schurawlewa; Zhurnal Obshchei Khimii; vol. 29; (1959); p. 1262; engl. Ausg. S. 1234 View in Reaxys

Rx-ID: 7446693 View in Reaxys 445/487 Yield

Conditions & References T= 90 °C Fordham; Williams; Canadian Journal of Research, Section B: Chemical Sciences; vol. 27; (1949); p. 943,947 View in Reaxys

S OO

Rx-ID: 7449882 View in Reaxys 446/487 Yield

Conditions & References T= 100 °C

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Hock; Lang; Chemische Berichte; vol. 77/79; (1944); p. 257,262 View in Reaxys O N

(v1)

Rx-ID: 11219561 View in Reaxys 447/487 Yield

Conditions & References Kinetics Baciocchi, Enrico; Bietti, Massimo; Di Fusco, Massimo; Lanzalunga, Osvaldo; Journal of Organic Chemistry; vol. 72; nb. 23; (2007); p. 8748 - 8754 View in Reaxys

Rx-ID: 40563 View in Reaxys 448/487 Yield

Conditions & References Grignard; Annales de Chimie (Cachan, France); vol. <7> 24; (1901); p. 468; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys Grignard; Annales de Chimie (Cachan, France); vol. <7> 24; (1901); p. 468; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys Grignard; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 624 View in Reaxys

O Na +

+Mg

I–

O–

Rx-ID: 532605 View in Reaxys 449/487 Yield

Conditions & References Salkind; Beburischwili; Chemische Berichte; vol. 42; (1909); p. 4502 View in Reaxys Patent; Bayer and Co.; DE166898 View in Reaxys Patent; Bayer and Co.; DE166899 View in Reaxys

O Na +

Br–

+Mg

O–

Rx-ID: 532606 View in Reaxys 450/487 Yield

Rx-ID: 715525 View in Reaxys 451/487

137/148

2016-05-12 16:14:46

Yield

Conditions & References Zersetzung mit Eiswasser und verd. Schwefelsaeure Grignard; Annales de Chimie (Cachan, France); vol. <7> 24; (1901); p. 468; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys Klages; Chemische Berichte; vol. 35; (1902); p. 2649; Chemische Berichte; vol. 39; (1906); p. 2591 View in Reaxys nachfolgend Zersetzung mit Eiswasser Grignard; Annales de Chimie (Cachan, France); vol. <7> 24; (1901); p. 468; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys Klages; Chemische Berichte; vol. 35; (1902); p. 2649; Chemische Berichte; vol. 39; (1906); p. 2591 View in Reaxys Klages; Chemische Berichte; vol. 35; (1902); p. 3507 View in Reaxys

O +Mg

I–

Rx-ID: 757977 View in Reaxys 452/487 Yield

O Br–

+Mg

Rx-ID: 757978 View in Reaxys 453/487 Yield

-1

S N+

F F (v6) F F P F F

H+

Rx-ID: 30170895 View in Reaxys 454/487 Yield

Conditions & References in acetonitrile, Photolysis, Inert atmosphere, Quantum yield, Kinetics Baciocchi, Enrico; Bettoni, Marta; Del Giacco, Tiziana; Lanzalunga, Osvaldo; Mazzonna, Marco; Mencarelli, Paolo; Journal of Organic Chemistry; vol. 76; nb. 2; (2011); p. 573 - 582

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View in Reaxys

-1

N+

F F (v6) F F P F F

H+

Rx-ID: 30170899 View in Reaxys 455/487 Yield

O HO

Rx-ID: 107978 View in Reaxys 456/487 Yield

Conditions & References Thermolysis Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys

O HO

Rx-ID: 129771 View in Reaxys 457/487 Yield

Conditions & References Thermolysis Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys

O HO

Rx-ID: 172939 View in Reaxys 458/487 Yield

Conditions & References Thermolysis Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys

O HO

Rx-ID: 218009 View in Reaxys 459/487 Yield

Conditions & References Thermolysis Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125

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View in Reaxys

Be Cl

Rx-ID: 614976 View in Reaxys 460/487 Yield

Conditions & References Gilman; Schulze; Journal of the Chemical Society; (1927); p. 2668 View in Reaxys Gilman; Schulze; Journal of the Chemical Society; (1927); p. 2668 View in Reaxys

Rx-ID: 639775 View in Reaxys 461/487 Yield

Conditions & References Thermolysis Kharasch et al.; Journal of Organic Chemistry; vol. 16; (1951); p. 113,125 View in Reaxys

+Mg

I–

Rx-ID: 716057 View in Reaxys 462/487 Yield

Conditions & References Grignard; Annales de Chimie (Cachan, France); vol. <7> 24; (1901); p. 468; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys Klages; Chemische Berichte; vol. 35; (1902); p. 2649; Chemische Berichte; vol. 39; (1906); p. 2591 View in Reaxys Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 130; (1900); p. 1324; Annales de Chimie (Cachan, France); vol. <7>24; (1901); p. 472; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys

Rx-ID: 742287 View in Reaxys 463/487 Yield

Conditions & References T= 50 - 64 °C , Rate constant Sokolow; Schuschunow; ; vol. 2; (1959); p. 29,33; ; (1960); p. 6275 View in Reaxys

N N

(v1)

N O

O N O

Rx-ID: 3378217 View in Reaxys 464/487 Yield

Conditions & References With metmyoglobin, var.: ferrous ion, Mechanism

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Griffin, Brenda Walker; Canadian Journal of Chemistry; vol. 60; (1982); p. 1463 - 1473 View in Reaxys OH

sodium amalgam HO

Rx-ID: 7542684 View in Reaxys 465/487 Yield

Conditions & References Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144 View in Reaxys

O +Mg

I–

Rx-ID: 40611 View in Reaxys 466/487 Yield

Conditions & References Grignard; Annales de Chimie (Cachan, France); vol. <7> 24; (1901); p. 468; Chem. Zentralbl.; vol. 72; nb. II; (1901); p. 623 View in Reaxys O O

+Mg

I–

Rx-ID: 281479 View in Reaxys 467/487 Yield

Conditions & References Matsubara; Perkin; Journal of the Chemical Society; vol. 87; (1905); p. 671 View in Reaxys

O +Mg

I–

Rx-ID: 614986 View in Reaxys 468/487 Yield

Conditions & References Tissier; Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 685 View in Reaxys O

+Mg

O O

I–

Rx-ID: 674255 View in Reaxys 469/487 Yield

Conditions & References Tissier; Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 685 View in Reaxys

HO HO

Rx-ID: 1999324 View in Reaxys 470/487

141/148

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Yield

O racemate

racemate

Rx-ID: 2017859 View in Reaxys 471/487 Yield

Conditions & References Time= 80h, T= 125 °C , reaction with different catalysts, different reaction times, Product distribution, Mechanism Lauterbach, Gerlinde; Pritzkow, W.; Tien, Tieu Dung; Voerckel, V.; Journal fuer Praktische Chemie (Leipzig); vol. 330; nb. 6; (1988); p. 933 - 946 View in Reaxys

SH P

S S

S P O

P S

Rx-ID: 3930242 View in Reaxys 472/487 Yield

Conditions & References in benzene, other dialkyl dithiophosphoric acids, other solvent; chemical polarization of nuclei, Product distribution, Mechanism Grossman, G.; Komber, G.; Kroshvitts, G.; Kirpichnikov, P. A.; Mukmeneva, N. A.; Pobedimskii, D. G.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 38; nb. 1.1; (1989); p. 26 - 32; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1989); p. 34 - 41 View in Reaxys

Rx-ID: 61073 View in Reaxys 473/487 Yield

Conditions & References λ: 254 nm und 313 nm.Photolysis Norrish; Searby; Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences; vol. 237; (1956); p. 464,471 View in Reaxys

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Rx-ID: 93446 View in Reaxys 474/487 Yield

Conditions & References Matsubara; Perkin; Journal of the Chemical Society; vol. 87; (1905); p. 671 View in Reaxys O O

Cl –

Rx-ID: 171370 View in Reaxys 475/487 Yield

Conditions & References Schmalfuss; Wetzeg; Journal fuer Praktische Chemie (Leipzig); vol. <2< 109 <1925>; p. 158 View in Reaxys

Rx-ID: 209289 View in Reaxys 476/487 Yield

Rx-ID: 609455 View in Reaxys 477/487 Yield

Conditions & References Tissier; Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 685 View in Reaxys O

O O

Rx-ID: 673903 View in Reaxys 478/487 Yield

Conditions & References Tissier; Grignard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 685 View in Reaxys OH O

sodium Cl

methyl-phenyl-ethylene oxide HO

Rx-ID: 7923864 View in Reaxys 479/487

143/148

2016-05-12 16:14:46

Yield

Conditions & References Tiffeneau; Annales de Chimie (Cachan, France); vol. <8>10; (1907); p. 190; Annales de Chimie (Cachan, France); vol. <8>11; (1907); p. 144 View in Reaxys

OH HO

S OO

Rx-ID: 7981091 View in Reaxys 480/487 Yield

Conditions & References Rotbart; Annales de Chimie (Cachan, France); vol. <11> 1; (1934); p. 439,503; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 197; (1933); p. 1225 View in Reaxys O O

magnesium O

Rx-ID: 7446251 View in Reaxys 481/487 Yield

Conditions & References Schlenk; Chemische Berichte; vol. 64; (1931); p. 739,743 View in Reaxys

-1 F F (v6) F F P F F

S N+

Rx-ID: 35718132 View in Reaxys 482/487 Yield

Conditions & References Flash photolysis, Kinetics Lanzalunga, Osvaldo; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 188; nb. 4; (2013); p. 322 330 View in Reaxys

–O

Pb4+

Rx-ID: 639774 View in Reaxys 483/487 Yield

Conditions & References Hock; Kropf; Chemische Berichte; vol. 91; (1958); p. 1681,1682, 1686 View in Reaxys

Rx-ID: 7157832 View in Reaxys 484/487 Yield 92 %

Conditions & References Patent; Fuchs, Philip; Lee, Seongmin; US2004/87820; (2004); (A1) English View in Reaxys

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Jeffery,E.A. et al.; Australian Journal of Chemistry; vol. 27; (1974); p. 2569 - 2576 View in Reaxys Duismann,W.; Ruechardt,C.; Chemische Berichte; vol. 106; (1973); p. 1083 - 1098 View in Reaxys Walling,C.; Padwa,A.; Journal of the American Chemical Society; vol. 85; (1963); p. 1593 - 1597 View in Reaxys Olah,G.A. et al.; Journal of the American Chemical Society; vol. 91; nb. 6; (1969); p. 1458 - 1469 View in Reaxys Wursthorn,K.R. et al.; Journal of the American Chemical Society; vol. 100; nb. 9; (1978); p. 2779 - 2789 View in Reaxys Farnum,D.G. et al.; Journal of the American Chemical Society; vol. 100; (1978); p. 3847 - 3855 View in Reaxys Collin,G. et al.; Justus Liebigs Annalen der Chemie; vol. 702; (1967); p. 55 - 67 View in Reaxys Koyama,K. et al.; Tetrahedron; vol. 23; (1967); p. 2665 - 2674 View in Reaxys Kharasch,M.S. et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1000 - 1006 View in Reaxys Traynelis,V.J. et al.; Journal of Organic Chemistry; vol. 27; (1962); p. 2377 - 2383 View in Reaxys Jones,L.B.; Foster,J.P.; Journal of Organic Chemistry; vol. 35; (1970); p. 1777 - 1781 View in Reaxys Verkade,P.E. et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 82; (1963); p. 637 - 650 View in Reaxys Blomberg,C.; Coops,J.; Recueil des Travaux Chimiques des Pays-Bas; vol. 83; (1964); p. 1083 - 1095 View in Reaxys Schaap,A.; Arense,J.F.; Recueil des Travaux Chimiques des Pays-Bas; vol. 87; (1968); p. 1249 - 1263 View in Reaxys Ito; Tokutake; Takamine Kenkyusho Nenpo; vol. 8; (1956); p. 47,50; ; (1958); p. 397 View in Reaxys Hadley; Halsall; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1974); p. 1334,1345 View in Reaxys Eliel; Rerick; Journal of the American Chemical Society; vol. 82; (1960); p. 1362,1365 View in Reaxys Kawabata et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3403,3406 View in Reaxys Sternerup; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 28; (1974); p. 579 View in Reaxys Kropf et al.; Justus Liebigs Annalen der Chemie; (1974); p. 1013 View in Reaxys Fomin et al.; Zhurnal Organicheskoi Khimii; vol. 7; (1971); p. 76,76,78 View in Reaxys Pasto; Snyder; Journal of Organic Chemistry; vol. 30; (1965); p. 1634,1635 View in Reaxys Henry-Basch et al.; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 260; (1965); p. 5809 View in Reaxys Ratcliff Jr.; Kochi; Journal of Organic Chemistry; vol. 37; (1972); p. 3268 View in Reaxys Brown; Peters; Journal of the American Chemical Society; vol. 99; (1977); p. 1712 View in Reaxys Sadikov et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 42; (1972); p. 1571,1563 View in Reaxys House et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 3067,3072 View in Reaxys Wang; Kingsbury; Journal of Organic Chemistry; vol. 37; (1972); p. 2489,2492 View in Reaxys Lapizkii et al.; Neftekhimiya; vol. 17; (1977); p. 563,566; ; vol. 87; nb. 167217; (1977) View in Reaxys Sapunow et al.; Neftekhimiya; vol. 19; (1979); p. 220,221

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View in Reaxys Min'kov; Keier; Kinetics and Catalysis; vol. 8; (1967); p. 133,134,135 View in Reaxys Ohkatsu et al.; Bulletin of the Chemical Society of Japan; vol. 51; (1978); p. 3606 View in Reaxys Bogat-skii et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 47; (1977); p. 2297,2095,2099 View in Reaxys Dumont et al.; Angewandte Chemie; vol. 86; (1974); p. 857 View in Reaxys Syper et al.; Roczniki Chemii; vol. 46; (1972); p. 849,850, 852 View in Reaxys Shchennikova et al.; Kinetika i Kataliz; vol. 9; (1968); p. 641,642 View in Reaxys Ishii et al.; Kogyo Kagaku Zasshi; vol. 64; (1961); p. 472; ; vol. 57; nb. 7149 View in Reaxys Tuzun; Yukseksik; Communications de la Faculte des Sciences de l'Universite d'Ankara, Serie B: Chimie; vol. 14; nb. 3; (1967); p. 34,35-52; ; vol. 70; nb. 67787a; (1969) View in Reaxys Patent; Allied Chem. Co.; BE626968; (1963); GB980272; (1963); ; vol. 61; nb. 612; (1964) View in Reaxys Alberola et al.; Anales de Quimica (1968-1979); vol. 72; (1976); p. 848 View in Reaxys Kelly; Spear; Australian Journal of Chemistry; vol. 31; (1978); p. 1209,1221 View in Reaxys Abenhaim; Namy; Tetrahedron Letters; (1972); p. 3011,3012 View in Reaxys Burghardt et al.; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 60; (1972); p. 3,4-7,9,10,12-17 View in Reaxys Kulicki; et al.; Zeszyty Naukowe Politechniki Slaskiej, Chemia; vol. 39; (1967); p. 67,71 View in Reaxys Maruyama et al.; Nippon Kagaku Zasshi; vol. 81; (1960); p. 1883; ; vol. 56; nb. 3385; (1962) View in Reaxys Yablokov et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 41; (1971); p. 1565,1570,1572 View in Reaxys Patent; Badische Anilin- und Soda-Fabrik A.G.; DE1275041; (1966); ; vol. 69; nb. 96208x; (1968) View in Reaxys Starowieyski et al.; Journal of Organometallic Chemistry; vol. 117; (1976); p. C1 View in Reaxys Norikov; Salukvadze; Doklady Physical Chemistry; vol. 203; (1972); p. 254 View in Reaxys Valendo et al.; Doklady Physical Chemistry; vol. 201; (1971); p. 1077 View in Reaxys Denney; Denney; Journal of the American Chemical Society; vol. 82; (1960); p. 1389,1393 View in Reaxys Pines; Schappell; Journal of Organic Chemistry; vol. 29; (1964); p. 1503,1507 View in Reaxys Kulicki; Stec; Roczniki Chemii; vol. 45; (1971); p. 601,602 View in Reaxys Macdonald; Shannon; Australian Journal of Chemistry; vol. 18; (1965); p. 1009,1014, 1015 View in Reaxys Sokolov et al.; Zhurnal Organicheskoi Khimii; vol. 8; (1972); p. 751,760 View in Reaxys Patent; Koninklijke Industrieele Maatschappij vorheen Noury + van der Lande, N.V.; BE613440; (1961); ; vol. 58; nb. 1402b; (1963) View in Reaxys Sano et al.; Nippon Kagaku Kaishi; (1972); p. 1699,1700,1701 View in Reaxys Neumann et al.; Chemische Berichte; vol. 100; (1967); p. 1063 View in Reaxys Laurent et al.; Bulletin de la Societe Chimique de France; (1967); p. 1995 View in Reaxys

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Fukui et al.; Bulletin of the Chemical Society of Japan; vol. 42; (1969); p. 312 View in Reaxys Razumovskij; Journal of Organic Chemistry USSR (English Translation); vol. 3; (1967); p. 756; Zhurnal Organicheskoi Khimii; vol. 3; (1967); p. 789 View in Reaxys Namy et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 268; (1969); p. 287 View in Reaxys Gaillard et al.; Bulletin de la Societe Chimique de France; (1967); p. 3360 View in Reaxys Smith; Waters; Journal of the Chemical Society [Section] B: Physical Organic; (1969); p. 462 View in Reaxys Raber et al.; Journal of the American Chemical Society; vol. 100; (1978); p. 8137,8139,8140,8142,8145,8146 View in Reaxys Alicyclic compounds such as: ... 2-Phenylethyl acetate; 1-Phenylethyl alcohol; 2-Phenylethyl alcohol; 2-Phenylethylamine; 2-Phenyl-2-propanol; 2-Methoxy-4-methylphenol; Patent; International Flavors and Fragrances Inc.; US4092333; (1978); (A1) English View in Reaxys Aromatic compounds such as: ... 2-Phenylethyl acetate 1-Phenylethyl alcohol 2-Phenylethyl alcohol 2-Phenylethylamine 2-Phenyl-2-propanol Patent; International Flavors and Fragrances Inc.; US4096158; (1978); (A1) English View in Reaxys The alcohols are illustrated by, but not limited to the following compounds. benzyl alcohol 2,4-di-ethyl benzyl alcohol 2-butyl alcohol α,α-dimethylbenzyl alcohol para-methyl benzyl alcohol 1,1-dimethyl hexyl alcohol α-phenyl ethyl alcohol Patent; The Goodyear Tire and Rubber Company; US4143076; (1979); (A1) English View in Reaxys 40 - 50 3; 22 %Chromat. in tetrahydrofuran Patent; Zeon Corporation; EP1405840; (2004); (A1) English View in Reaxys

Rx-ID: 24521645 View in Reaxys 485/487 Yield 30.6%

Conditions & References IV : EXAMPLE IV

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EXAMPLE IV The procedure of Example III was repeated, but this time cumene (0.056 moles) and hydrogen peroxide (35percent, 0.22 moles) were used. The reaction mixture, analyzed by HPLC, revealed that 87.4percent of the cumene had been consumed, yielding products including acetophenone (43.1percent yield) and 2-phenyl-2-propanol (30.6percent yield). Patent; Solvay Interox Limited; US5473101; (1995); (A1) English View in Reaxys

Rx-ID: 23938152 View in Reaxys 486/487 Yield

Conditions & References

10.4%

2 : EXAMPLE 2 (NOT ACCORDING TO THE INVENTION, USING COCATALYST) EXAMPLE 2 (NOT ACCORDING TO THE INVENTION, USING COCATALYST) In a round-bottom flask fitted with superposed reflux condenser, 30 mmol of cumene are admixed at a temperature of 125° C. with 0.3 mmol of N-hydroxyphthalimide and 0.3 mmol of cobalt(II) acetate. The reaction mixture is stirred at the specified temperature under an oxygen atmosphere of 1 bar for 8 hours. The target product is not formed, but instead acetophenone with a selectivity of 58.7percent, 2-phenyl-2-propanol (13.1percent) and phenol (10.4percent) are obtained at a cumene conversion of 49.3percent. Patent; Kuhnle, Adolf; Duda, Mark; Tanger, Uwe; Sheldon, Roger Arthur; Manickam, Sasidharan; Arends, Isabella W.C.E.; US2003/83527; (2003); (A1) English View in Reaxys

Rx-ID: 22897607 View in Reaxys 487/487 Yield 64 %, 19 %, 10 %

Conditions & References Patent; Fuchs, Philip; Lee, Seongmin; US2004/87820; (2004); (A1) English View in Reaxys

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