Elimination reactions. Part I. Reaction of bis-(4-nitrophenyl)methyl chloride with sodium hydroxide in aqueous dioxan

Abstract

The reaction between bis-(4-nitrophenyl)methyl chloride and sodium hydroxide in aqueous dioxan under air gives tetrakis-4-nitrophenylethylene and 4,4′-dinitrobenzophenone, whereas the reaction under nitrogen yields the ethylene as the sole product. The carbanion formed in the fast and reversible base-catalysed α-proton extraction from bis-(4-nitrophenyl)methyl chloride attacks aldehydes of different reactivities, under nitrogen, to yield the corresponding epoxides, the order of reactivity of the benzaldehydes used being 4-NO₂ > 3-NO₂ > 2-NO₂ > H > 4-OMe. The kinetics show first-order dependence upon the chloride and possible reaction mechanisms are discussed.