Unexpected Reaction of Dimethyl Acetylenedicarboxylate with in Situ Generated Arylketenes Catalyzed by 1-Methylimidazole

Abstract

[reaction: see text]. An unexpected 1-methylimidazole-catalyzed reaction of dimethyl acetylenedicarboxylate (DMAD) with in situ generated arylketenes leading to the synthesis of dimethyl 2-arylidenesuccinates under mild conditions is described. A plausible mechanism has been proposed.