Oxidation with Potassium Peroxysulfate

A solution of 18.44 g of Oxone (49.5% KHSO5) in 40 mL of water is added to a cooled (0 °C) solution of 1.24 g (0.01 mol) of methyl phenyl sulfide in 40 mL of methanol. The resulting cloudy slurry is stirred for 4 h at room temperature, diluted with water, and extracted 3 times with chloroform. The combined extracts are washed with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a quantitative yield of methyl phenyl sulfone as a white solid. Recrystallization yields 95% of pure methyl phenyl sulfone, mp 85-88.5 °C. 

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Like tertiary amines, tertiary phosphines are readily transformed into the corresponding oxides, phosphine oxides. Tributylphosphine in di-chloromethane is oxidized with ozone adsorbed on silica gel at -70 "C to tributylphosphine oxide in 92% yield [113]. Other oxidants used to transform phosphines into phosphine oxides are potassium peroxysulfate [205], argentic oxide [381 ], manganese dioxide [813], and barium manganate [S55] (equation 537). 

Among other remarkable developments, it should be noted that the carboxylation of methane can be coupled with oxidation by potassium peroxysulfate in trifluoro-acetic acid to yield acetic acid, the reaction being catalyzed by Cu(OAc)2 ... 

Neutral aqueous salt solutions react slowly with tin when oxygen is present but oxidizing salt solutions, such as potassium peroxysulfate, ferric chloride and sulfate, and aluminum and stannic chlorides dissolve tin. Nonaqueous organic solvents, lubricating oils, and gasoline have Httle effect. 

Silver (II) oxide [1301-96-8] M 123.9, m >100 (dec), d 7.22. Soluble in 40,000 parts of H2O, and should be protected from light. Stir with an alkaline solution of potassium peroxysulfate (K2S2O8) at 85-... 

Oxidants suitable for the partial oxidation of amines to nitroso compounds are peroxy acids Caro acid, which is prepared in situ from potassium persulfate and sulfuric acid [195, 199 potassium peroxysulfate (Oxone) [295] peroxyacetic acid [i53], and peroxybenzoic add [1186], 3-Nitro-o-toluidine [195] and 5-nitro-o-toluidine [199] in aqueous-alcoholic solutions, when treated with a mixture of potassium persulfate and concentrated sulfuric acid, give 3-nitro-2-nitrosotoluene and 5-nitro-2-nitrosotoluene in respective yields of 60 and 55-66%. Organic peroxy acids convert 2,6-dihaloanilines into 2,6-dihalonitrosobenzenes (equation 497) [753, 1186]. p-Phenylenediamine (1,4-diaminobenzene) is oxidized by Oxone (2KHS05 KHS04 K2S04) in an aqueous suspension at room temperature to p-dinitrosobenzene in a quantitative yield [205]. 

Colupulone is hydroxylated to 4-hydroxycolupulone (267, Fig. 110) upon treatment with potassium hydrogen peroxysulfate ("Caroat") in aqueous alkaline buffers. Peracids, such as m.-chloroperbenzoic acid or peracetic acid, can also be applied. Compound 267 is stable at room temperature over a period of months, but it is readily isomerized in NaOH 0.01 N to 5-(3-methyl-2-butenyl)isocohumulone (268, Fig. 110). Characterization is evident from the spectrometric data. Upon boiling of 268 for a short time in alkaline solution, 5-(3-methyl-2-butenyl)cohumulinic acid or dihydrocohulupone (202, Fig. 85) is obtained. This compound is also accessible by reduction of cohulupone with sodium borohydride (see 13.1.1.2.1.) (22). None of the three oxidized products leads to cohulupone in auto-oxidation reaction conditions. This confirms the proposed mechanism of formation of cohulupone via 4-hydroperoxycolupulone (see 13.1.1.1.2.). 

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