Diels-Alder reaction of 2-cyano-1-azadienes. The effect of nitrogen substituents

…, SD Kuduk, FW Fowler, DS Grierson

Index: Trione, Celine; Toledo, Leticia M.; Kuduk, Scott D.; Fowler, Frank W.; Grierson, David S. Journal of Organic Chemistry, 1993 , vol. 58, # 8 p. 2075 - 2080

Full Text: HTML

Citation Number: 44

Abstract

The Diels-Alder reactions of 2-cyano-1-aza dienes with three nitrogen substituents possessing different electronic requirements (phenyl, C02CzH5, and OCH3) were studied with three dienophiles with different electronic requirements (styrene, methyl acrylate, and ethyl vinyl ether). The N-phenyl substituent aza diene was equally reactive with all three dienophiles. The N-CO&2H5-substituted aza diene behaved as an electrophilic diene ...