The N-ethylbenzisoxazolium cation—II: The mechanism of reactions of the cation with nucleophiles

DS Kemp

Index: Kemp,D.S. Tetrahedron, 1967 , vol. 23, p. 2001 - 2015

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Citation Number: 13

Abstract

The N-ethylbenzisoxazolium cation has been shown to undergo a ready general base- catalyzed internal elimination to form a transitory N-ethylbenzoketoketenimine. Alternative pathways involving benzoisoxazolines have been excluded by kinetic evidence and by study of the model substance, 2-ethylbenzo-4-isoxazoline. A competition study has shown that the intermediate benzoketoketenimine exhibits high selectivity in many of its ...