A. Kirby, G. J. Lloyd
Aug 20, 1974
Citations
0
Influential Citations
4
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
The hydrolysis of the anion of 2-carboxyphenyl 4-hydroxybutyrate at 39° is 85 times faster than that of aspirin anion, and some 500 times faster than the spontaneous hydrolysis of phenyl 4-hydroxybutyrate. The expected mechanism is concerted intramolecular general base–intramolecular nucleophilic catalysis, by the carboxylate and hydroxy-groups, respectively, and the expected products are salicylate and γ-butyrolactone. All the evidence is consistent with this mechanism, which constitutes the first clear-cut example of bifunctional catalysis of ester hydrolysis.