Carbon-Carbon Alkylations with Amines and Ammonium Salts

Abstract

This chapter is a review of those reactions of compounds containing labile amino groups in which a carbon-carbon bond is formed by amine replacement as, for example, in the alkylation of diethyl malonate by 1-dimethylamino-3-butanone. Attention has been given primarily to reactions of amines prepared by the Mannich reaction (Mannich bases), but for comparison, analogous reactions of simpler quaternary ammonium salts have been included. Keywords: carbon-carbon alkylations; amines; ammonium salts; cyanide; replacements; active methyl groups; active methylene groups; indole; quaternary salts; organometallic compounds; related reactions; experimental conditions