Elimination reactions. Part II. Base-catalysed formation of stilbene derivatives from α-phenyl- and α-(4-nitrobenzyl)-substituted 4-nitrobenzyl chloride

Abstract

The reactions of 4-nitrophenyl(phenyl)methyl chloride and 1,2-bis-(4-nitrophenyl)ethyl chloride with sodium hydroxide in aqueous dioxan have been studied, and shown to yield stilbene derivatives. The overall rate of reaction of the former is slower than that of 4-nitrobenzyl chloride under the same conditions, presumably because of the stabilization of the carbanion by the extra phenyl group, whereas the latter compound reacts ca. 5 times faster than 4-nitrobenzyl chloride. The results imply that, in the absence of oxygen, the reactions do not occur via radical pathways.