Nitration of fully methylated acylbenzenes and 1,3-diacylbenzenes bearing bulky acyl groups. Side-chain attack occurring exclusively on the methyl group at the most hindered site

Abstract

On treatment with concentrated nitric acid, the title compounds undergo attack on the side-chain which occurs exclusively on the methyl group at the most hindered site, giving 6-acyl-2,3,4,5-tetramethylbenzyl nitrate, and 2,6-diacyl-3,4,5-trimethylphenylnitromethane and/or 2,6-diacyl-3,4,5-trimethylbenzyl nitrate as the respective major side-chain substitution products.