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.
A. F. Gerrard and N. K. Hamer, J. Chem. Soc. B, 1967, 1122 DOI: 10.1039/J29670001122
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