DECARBOXYLATION OF 6-NITROBENZISOXAZOLE-3-CARBOXYLATE ION IN DICHLOROMETHANE - THE EFFECTS OF SURFACTANT STRUCTURE

The spontaneous decarboxylation of the 6-nitrobenzisoxazole-3-carboxyl ate ion, 1, in dichloromethane is catalyzed by amine oxide surfactants , C(14)H(29)N(+)R(2)O(-), R = Me, n -Pr, and less strongly by betaine sulfonate surfactants. The amine oxides are sufficiently basic in the solvent to deprotonate the carboxylic acid, Solutions of the amine oxi des tolerate water which, as with cationic surfactants, sharply inhibi ts reaction, but solutions of C(14)H(29)N(+)R(2)SO(3)(-), R = Me, n -P r, will not tolerate water, The water inhibitions are probably due to formation of ''water-pool'' reverse micelles which are catalytically l ess effective than small surfactant clusters. (C) 1996 Academic Press, Inc.