Elimination and addition reactions. Part XXVII. Addition of amides to electrophilic alkenes

Abstract

Treatment of amides from primary amines with strong bases and electrophilic alkenes (acrylonitrile or p-tolyl vinyl sulphone) gives products derived from N-alkylation of the amide. When amides without an N–H bond are used, no reaction occurs unless the amide gives a stabilised carbanion on proton abstraction; C-alkylation then occurs. When N- and C-alkylation can compete, N-alkylation is preferred.

Dialkylation of diamides occurs readily, and evidence for alkylation of a low molecular weight polyamide has been obtained. Alkylation of Nylon 6 and Nylon 66, however, does not occur to an appreciable extent under the conditions used for the other amides.