Evidence for a planar intermediate in alkaline solvolysis of methyl N-cyclohexylphosphoramidothioic chloride

Abstract

The synthesis of methyl N-cyclohexylphosphoramidothioic chloride is reported and its solvolysis is studied. In aqueous dimethoxyethane the rate of neutral hydrolysis is 1/13 the corresponding rate of dimethyl phosphorochloridothioate whereas the rate of alkaline hydrolysis is 45,000 times faster. Unlike the neutral hydrolysis which is shown to be stereospecific, the alkaline hydrolysis gives a racemic product which must result from a symmetrical intermediate. This intermediate is considered to be the analogue of a monomeric metaphosphate.