OXIDATIVE PROPERTIES OF TRIFLIC ANHYDRIDE - OXIDATION OF ALCOHOLS ANDSULFIDES

The reaction of dimethyl sulfide with triflic anhydride leads to the f ormation of the corresponding dimethyl(trifluoromethanesulfonyl)sulfon ium salt. The latter can be used in the mild oxidation of primary and secondary alcohols including unsaturated and natural ones to the corre sponding carbonyl compounds in 34-75% yield. The reaction of various s ulfides with triflic anhydride was studied. It was found that the reac tions give rise to the corresponding dialkyl(trifluoromethanesulfonyl) sulfonium salts. Succeeding treatment with water leads to the formatio n of sulfoxides in 25-73% yield. Formation of sulfones does not procee d.