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

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

全文：HTML全文

被引用次数: 130

摘要

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, ...