α-Acetyl- and α-Cyanovinyl 2,4-Dinitrophenyl Carboxylate as Useful Ketene Equivalents for the Diels-Alder Reaction

David I. MaGee; May Ling Lee

doi:10.1055/s-1997-5775

Synlett 1997; 1997(7): 786-788
DOI: 10.1055/s-1997-5775

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α-Acetyl- and α-Cyanovinyl 2,4-Dinitrophenyl Carboxylate as Useful Ketene Equivalents for the Diels-Alder Reaction

David I. MaGee^* , May Ling Lee

^*Department of Chemistry, University of New Brunswick, Bag Service #45222, Fredericton, New Brunswick, Canada, E3B 6E2, Fax 506-453-4981; email DMagee@unb.ca

Abstract

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Two ketene equivalents (5 and 35) have been developed for use in the Diels-Alder reaction. These dienophiles exhibit a marked increase in reactivity in comparison with the more conventional acetoxyacrylonitrile. Conversions of the cycloadducts to the requisite ketones occurs under mild, and moderate to high yielding conditions.

Diels-Alder - reactive ketene equivalents

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