Inversion of chirality at sulphinyl sulphur in a reaction not involving breaking of bonds of the chiral sulphur atom

Abstract

Conversion of (+)-methyl p-tolyl sulphoxide into the corresponding (–)- or (+)-α-halogenomethyl derivatives in the presence or in the absence of silver nitrate, respectively, involves inversion of configuration at sulphur in one of the two reactions; the inversion was proved to occur without any breaking of bonds at the chiral centre or any diastereomeric interaction in the transition state.