Amine oxidation. Part I. The oxidation of NN-dimethylaniline to crystal violet and methyl violet

Abstract

The oxidation of NN-dimethylaniline by cupric chloride or by chloranil gives N-p-dimethylaminobenzyl-N-methylaniline, 4,4′-bisdimethylaminodiphenylmethane, crystal violet, and methyl violet. A detailed study of the oxidation by cupric chloride has provided evidence that the first two products are intermediates in the formation of the violet dyes and has revealed other features which bear on the reaction mechanism.