Heterogeneous reactions with organic solids. Part I. The stereospecific dehydrohalogenation of solid β,β′-dihalogenoadipates by gaseous amines

Abstract

Solid dimethyl and dibenzyl esters of meso-β,β′-dichloro- and meso-β,β′-dibromo-adipates react quantitatively with gaseous dry ammonia, methylamine, and dimethylamine, yielding stereospecifically the corresponding diesters of trans,trans-hexa-2,4-dienedioic acid. When the same reactants were combined in ethanol or dimethylformamide solutions, a mixture of 2,4-trans,cis- and trans,trans-diesters and -diamides was obtained. Possible routes for the reaction are discussed.