Reactions of anions of N-benzylidenebenzylamines and related compounds. A simple route to α-substituted benzylamines

Abstract

The generation of anions of substituted N-benzylidenebenzylamines and some pyridinoid analogues is described. The site of alkylation of the ambident anion is critically dependent upon the nature and pattern of ring substitution. Anions derived from N-mesitylidenebenzylamines react with alkyl halides and ethyl chloroformate main or exclusively at the carbon atom α to the aryl group originating from the benzylamine precursor. The synthetic implications of the study are discussed.