Journal of the American Chemical Society

Intramolecular nucleophilic addition of phenolate oxygen to double bonds activated by carboxyl and carboxylate groups. Relative reactivity, stereochemistry, and …

TL Amyes, AJ Kirby

Index: Amyes, Tina L.; Kirby, Anthony J. Journal of the American Chemical Society, 1988 , vol. 110, # 19 p. 6505 - 6514

Full Text: HTML

Citation Number: 16

Abstract

Abstract: The cyclization reactions of substituted 4-methyl-4-(2-hydroxyphenyl) pent-2-enoic acid derivatives (7) in water involve intramolecular nucleophilic attack of phenolate oxygen on the activated double bond. Activation by COO-and COOH groups gives rate enhancements over a hydrogen substituent of 4000 and IO8, respectively, for the unsubstituted acid. Both mono-and dianion reactions are general-acid-catalyzed by ...