The orienting influence of the methyl group in toluene in the gomberg reaction

Abstract

When diazotized 6‐nitro‐m‐toluidine (Me = 1) reacts with toluene, substitution occurs in the ortho‐and meta‐positions in the toluene, to give 3:2′‐dimethyl‐4‐nitrodiphenyl and 3: 3′‐dimethyl‐4‐nitrodiphenyl. The proportion of meta‐substitution is greater than that observed in electrophilic substitutionreactions with toluene, confirming conclusions drawn from the quantum‐mechanical analysis of Wheland (1942).