Mechanism of the rapid alkaline hydrolysis of a phosphoramidothioate ester
Abstract
The relative rates and the stereochemistry of alkaline hydrolysis of methyl p-nitrophenyl N-cyclohexyl-phosphoramidothioate and -phosphoromorpholidothioate are reported. Despite a considerable difference in rate, both reactions show similar stereospecificity. The interpretation of these observations in relation to a metaphosphate-type intermediate in the former case is discussed.