Anodic acetamidosulphenylation of alkenes via anodic oxidation of disulphides

Abstract

Anodic oxidation, at platinum and carbon electrodes, of dimethyl, diphenyl, dibenzyl, and heterocyclic disulphides in acetonitrile in the presence of alkenes affords products of acetamidosulphenylation. With cyclic alkenes a high selectivity for trans-addition is observed. With terminal alkenes the terminal sulphides are formed with high regioselectivity. The mechanism of addition is discussed in the light of product and electroanalytical studies.