Reaction of 4-nitrobenzyl and 4-nitrophenyl(phenyl)methyl halides with potassium t-butoxide

Abstract

The reactions of 4-nitrobenzyl and 4 nitrophenyl(phenyl)methyl halides with t-butoxide in t-butyl alcohol solution give high yields of 4,4′-dinitrostilbene and 4,4′-dinitrotetraphenylethylene respectively. The initial reaction is the production of the carbanion which subsequently reacts in a first-order reaction. Evidence is presented which supports a radical anion chain mechanism for the reactions both in the presence and the absence of oxygen.