Sulfides with hydrogen peroxide

Another difference between sulfides and ethers is that sulfides are easily oxidized. Treatment of a sulfide with hydrogen peroxide, H202, at room temperature yields the corresponding sulfoxide (R2SO), and further oxidation of the sulfoxide with a peroxyacid yields a sulfone (R2S02)-... 

ASYMMETRIC SULFOXIDATION OF ARYL METHYL SULFIDES WITH HYDROGEN PEROXIDE IN WATER... 

Figure 8. The activity of different catalysts in oxidation of n-dibutyl sulfide with hydrogen peroxide.

Trevisan V, Signoretto M, Colonna S, Pironti V, Strukul G (2004) Microencapsulated Chloroperoxidase as a Recyclable Catalyst for the Enantioselective Oxidation of Sulfides with Hydrogen Peroxide. Angew Chem Int Ed 43 4097... 

The oxidation of methyl phenyl sulfide with hydrogen peroxide, in the presence of ammonium hydrogencarbonate, takes place by a mechanism involving HCO4-... 

Methyl />-tolyl sulfone has been prepared by oxidation of methyl 7>-tolyl sulfide with hydrogen peroxide 4 r or ruthenium tetroxide,6 by alkylation of sodium -toluenesullinate with methyl iodide 7,8 or with methyl potassium sulfate,9 by decarboxylation of -tolylsulfonylacetic acid,7 by thermal decomposition of tetramethylammonium -toluenesulfinate,10 by reaction of cw-bis-(%tolylsulfonvl)-ethene with sodium hydroxide (low yield),11 by the reaction of methanesulfonyl chloride with toluene in the presence of aluminum chloride (mixture of isomers),12 by... 

Figure 3.101 Manganese salen catalyst for diastereoselective oxidation of sulfides with hydrogen peroxide.

Figure 5.8 Reactions of hydrogen sulfide with hydrogen peroxide at various pH values.

Oxidation of dipyrazinyl sulfide with hydrogen peroxide in acetic acid gave dipyrazin-2-yl sulfone (821). 

Oxidation of organic sulfides with hydrogen peroxide, over Ti-containing zeolites, may be a selective, mild and facile method for preparing sulfoxides. The reactivity of thioethers is in... 

The Swern oxidation of alcohols to aldehydes is carried out with dimethyl sulfoxide. A polymeric version (5.53) used poly(hexylene sulfoxide), obtained by the oxidation of the corresponding sulfide with hydrogen peroxide to facilitate recovery and reuse, at the same time the bad smell of dimethyl sulfide was avoided. Quantitative yields were... 

Diphenyldiethylsulfoxide was obtained by oxidation of the corresponding sulfide with hydrogen peroxide and served as a model for the preventive antioxidant after its action as a hydroperoxide decomposer. 

As mentioned before (Section 7.2.1), aqueous hydrogen peroxide is an ecofriendly and versatile reagent. Thus, as shown in Scheme 7.8, Katsuki used chiral titanium-salen catalyst 12 for the oxidation of sulfides with hydrogen peroxide or urea-hydrogen peroxide adduct (UHP). Under these mild reaction conditions, chiral sulfoxides were obtained in good yields with high enantioselectivities. 

SuUone (Section 16.16) R—SO2—R, the final product of oxidation of a sulfide with hydrogen peroxide. 

The sulfoxide complexes 138a-c were prepared by oxidation of the corresponding sulfides with hydrogen peroxide. ... 

In oxidation reaction of sulfides with hydrogen peroxide, ZrCU was used as a promoter of the reaction. As shown in Equation 79, benzyl sulfide (180) was selectively converted into the corresponding sulfoxide (181) or sulfone (182), almost... 

Overall, Schiff-based V complexes catalyzed asymmetric oxidation of sulfides with hydrogen peroxide represents one of the best methods in terms of high yields and enantioselectivity, low catalyst loading and simple preparation of the catalyst, as well as employment of ligands from relatively cheap chiral building blocks. 

Also obtained by oxidation of 3,3 -diacetyl-4,4 -dihydroxydiphenyl sulfide with hydrogen peroxide (73%) [5915] according to [5921] or with 30% hydrogen peroxide in acetic acid at r.t. for 48 h (63%) [5922],... 

Obtained by oxidation of 2,2 -dihydroxy-5,5 -dipropiony-Idiphenyl sulfide with hydrogen peroxide (100 vols.) in acetone at r.t. overnight (73%) [6550]. 

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