Intramolecular catalysis in cis??diethyl 2??carboxyvinylphosphonate hydrolysis

JPJ van der Holst, C van Hooidonk…

Index: van der Holst,J.P.J. et al. Recueil des Travaux Chimiques des Pays-Bas, 1974 , vol. 93, p. 40 - 43

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Abstract

Abstract The hydrolysis of the title compound proceeds very fast in weakly acidic aqueous media by a stepwise release of both ethyl ester groups via phosphorus-oxygen bond fission. The reactions are about 10 6 times faster than that for the release of one ethyl group of the corresponding trans-isomer. The observed kinetics are consistent with a mechanism involving intramolecular catalysis by the undissociated carboxyl group.