Oxidative Properties of Triflic Anhydride. Oxidation of Alcohols and Sulfides

Abstract

The reaction of dimethyl sulfide with triflic anhydride leads to the formation of the corresponding dimethyl(trifluoromethanesulfonyl)sulfonium salt. The latter can be used in the mild oxidation of primary and secondary alcohols including unsaturated and natural ones to the corresponding carbonyl compounds in 34-75% yield. The reaction of various sulfides with triflic anhydride was studied. It was found that the reactions give rise to the corresponding dialkyl(trifluoromethanesulfonyl)sulfonium salts. Succeeding treatment with water leads to the formation of sulfoxides in 25-73% yield. Formation of sulfones does not proceed.