Side-chain reactions of 2,4,5-trimethylneopentylbenzene with nitric acid and with cerium ammonium nitrate: comparison of the products from reactions via arenium ions and via cation radicals

Abstract

When treated with excess of nitric acid, the title arene underwent both nitro-oxylation of the methyl group and isomerization of the neopentyl group, followed by nitration, giving 3-(4,5-dimethyl-2-nitro-oxymethylphenyl)-2-methyl-1-nitrobut-2-ene as the major product, while with cerium ammonium nitrate it yielded a mixture of isomeric benzyl nitrates; these results show that side chain substitutions of arenium ions and cation radicals follow different pathways.