Synthesis

Reactions of 2-(dialkylamino) arylacetonitriles with acetylenes under basic conditions. A simple synthesis of substituted mono and diketones

T Zdrojewski, A Jończyk

Index: Zdrojewski, T.; Jonczyk, A. Synthesis, 1990 , # 3 p. 224 - 233

Full Text: HTML

Citation Number: 8

Abstract

Furthermore we have found that amino nitrile carbanions add readily to C-1 of ethoxyacetylene (2 c). In these cases, the simple vinyl derivatives 15 were formed exclusively. Further reactions of 15 with 8, the anion of 1, have not been observed (Scheme F, Table 1). This fact may be explained by the resonance structure 15', in which the negative charge on C-3 hampers the attack of the nucleophile.