Side chain nitration of polymethylbenzenes in nitric acid-acetic anhydride mixtures

Abstract

Product distributions resulting from nitration of polymethylbenzenes in nitric acid-acetic anhydride mixtures have been determined by gas chromatography. Nitration of a methyl group occurs in all the substrates studied; such nitration occurs only at a methyl group para to the methyl most activated to ipso nitration. These results support the view that side chain nitration occurs through the diene intermediates which lead to ring acetoxylation.