Interaction between electron donor and acceptor groups in some trisubstituted benzenes. Part 1. Relative reactivities of 4-substituted 1,2-dinitrobenzenes towards sodium methoxide

Abstract

In an effort to study the effects of ‘through conjugation’ on the properties of some 1,2,4-trisubstituted benzenes, the rates of reaction of a series of four 4-substituted 1,2-dinitrobenzenes with sodium methoxide in methanol have been studied. Although reactivities at the 2-position were qualitatively in the order to be expected from inductive effects, those at the 1-position were highly sensitive to the influence of mesomeric donor action of the 4-substituent. Relatively large effects were seen for the 4-alkyl derivatives; and C–H hyperconjugation appeared to be stronger than C–C hyperconjugation.