The Electrochemical Oxidation of N,N-Dimethylaniline

Abstract

The electrochemical oxidation of N,N‐dimethylaniline (DMA) has been investigated in nonaqueous media in some detail. The products formed were found to depend on DMA concentration and the time of electrolysis. At low concentrations (10−3M), the main product formed is N,N,N',N'‐tetramethylbenzidine. At intermediate concentrations (10−2M) the major product is 4,4'‐methylenebis (N,N‐dimethylaniline), and at higher concentrations, especially at longer electrolysis times, the dye crystal violet and its leuco form were produced in large amounts. The mechanism to form these products depends on the lability of the methyl groups on the amine nitrogen; when other N,N‐dialkylanilines were electrolyzed under similar conditions, only the corresponding tetraalkylbenzidines could be isolated.