Anodic oxidation of di-tert-butyl disulfide: a facile method for the preparation of N-tert-butylamides

Abstract

The electrochemical oxidation of di-tert-butyl disulfide is shown to correspond to a one electron process; at 1.3 V, one carbon–sulfur bond is cleaved yielding two intermediate special : the tret-butyl cation and the radical Bu^tS–S˙; a Ritter reaction occurs with the cation when the sovent is a nitrile and the cation dimerizes in to a tetrasulfide; at a more positive potential (1.9V) the two carbon–sulfur bonds are cleaved giving Bu^t+ and sulfur.