Metal catalysis in oxidation by peroxides. 28. Kinetics and mechanism of the molybdenum-catalyzed oxidation of sulfoxides to sulfones with hydrogen peroxide

Abstract

The rates of oxidation to sulfones of three model sulfoxides, di-n-butyl, phenyl methyl, and diphenyl, with hydrogen peroxide, in the presence of catalytic amounts of MoO2(acac) 2, have been measured in ethanol solvent, at 40 ΰC, both in acid and basic solutions. The comparison of the behavior observed with those of the mchloroperbenzoic oxidation of the same substrates, either in acid or basic solutions, and of the oxidation of the parent sulfides provides an useful mechanistic tool for differentiating electrophilic oxygen transfers from the nucleophilic ones. © 1987, American Chemical Society. All rights reserved.