Physical organic chemistry of benzisoxazoles. IV. Origins and catalytic nature of the solvent rate acceleration for the decarboxylation of 3-carboxybenzisoxazoles

DS Kemp, DD Cox, KG Paul

Index: Kemp,D.S. et al. Journal of the American Chemical Society, 1975 , vol. 97, p. 7312 - 7318

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Citation Number: 130

Abstract

Abstract: Benzisoxazoles bearing 3-hydrogens isomerize to salicylonitriles in the presence of tetrabutylammonium acetate in dipolar aprotic solvents at rates which are up to 10'times larger than those observed in water. The decarboxylation of salts of 3-carboxy-6- nitrobenzisoxazole in water is accelerated by as much as IO4 by the addition of a benzonitrile phase. In striking contrast to the behavior of other 3-carboxybenzisoxazoles, ...