The reaction of ethenetetracarbonitrile with acyclic β-dicarbonyl compounds and related studies

Abstract

The reaction of ethenetetracarbonitrile (TCNE) with acyclic β- dicarbonyl compounds has been shown to give 2-dicyanomethylene-2,5- dihydropyrroles (5) via 2-imino-2,3-dihydrofurans (4). Hydrogenation of (5) gave the pyrroles (16). Representative pyrroles were degraded and synthesized by an alternative route. The novel transformation of substituted malononitriles to carboxylic acids has been investigated. The reaction of alcohols with ketone-ethenetetracarbonitrile adducts has been reinvestigated.