Reactivity and selectivity in the oxidation of aryl methyl sulfides and sulfoxides by hydrogen peroxide mediated by acetonitrile

Abstract

In homogeneous methanol solution containing potassium carbonate, hydrogen peroxide and acetonitrile, the active oxidant in the conversion of p-substituted-phenyl methyl sulfides into the sulfoxides is selective (ρ=–1.0 at 0 °C) but the oxidation of the related sulfoxides at 0 and 24 °C shows low selectivity, which, taken in conjunction with direct kinetic data, throws new light on the active oxidizing species in these nitrile-mediated reactions.