Oxidations with Iodosobenzene Diacetate. VII. The oxidation of p-Nitro-N-methylaniline

Abstract

The reaction of p-nitro-N-methylaniline with iodosobenzene diacetate has been investigated in both benzene and acetic acid solution. The relative amount of the oxidant has been varied. The nature of the products indicates that extensive demethylation occurs. Tetramethylbenzidine is formed when dimethylaniline is oxidized in benzene. The mechanisms of these reactions are discussed.