Concepedia

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

Hanfeng Ding, Cheng Ma, Yewei Yang, Yanguang Wang

Organic Letters · 2005 · 31 citations · 16 references

DOI

Concepts

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.

References

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Novel Pyridine-Catalyzed Reaction of Dimethyl Acetylenedicarboxylate with Aldehydes:  Formal [2 + 2] Cycloaddition Leading to 2-Oxo-3-benzylidinesuccinates

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