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Issue 13, 1975
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Differences in mechanisms of nucleophilic substitution at phosphorus in S-alkyl alkylphosphonothioates and S-alkyl phosphorothioates

Abstract

Whereas most phosphono-derivatives are hydrolysed more rapidly by hydroxide than the corresponding phosphoro-derivatives, the reverse situation holds for S-alkyl phosphonothioates and S-alkyl phosphorothioates; this reversal of the more usual pattern may be related to a stereochemical difference in that nucleophilic substitution in S-alkyl alkylphosphonothioates proceeds with inversion of configuration, whereas retention of configuration is observed for similar reactions with S-alkyl phosphorothioates.

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Article information


J. Chem. Soc., Chem. Commun., 1975, 500-501
Article type
Paper

Differences in mechanisms of nucleophilic substitution at phosphorus in S-alkyl alkylphosphonothioates and S-alkyl phosphorothioates

T. D. Inch, G. J. Lewis, R. G. Wilkinson and P. Watts, J. Chem. Soc., Chem. Commun., 1975, 500
DOI: 10.1039/C39750000500

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