The hydrolysis of phosphate esters

Abstract

The hydrolysis of a phosphate, phosphonate or phosphinate ester generally takes place either through a trigonal bipyramidal hydroxyphosphorane as intermediate (with expansion of the coordination number of phosphorus from four to five) or (at least for phosphates) through a monomeric metaphosphate as intermediate (with contraction of the coordination number of phosphorus from four to three). These processes parallel the principal mechanisms for the hydrolysis of carboxylic esters, which require either the formation of a tetrahedral intermediate or that of an acylium cation. © 1977, Walter de Gruyter. All rights reserved.