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DOI: 10.1039/A806926C (Paper) Reference Section for: Chem. Commun., 1998, 2339-2340

Stereochemical evidence for elimination–addition and a methylenethioxophosphorane (thiophosphene) intermediate in nucleophilic substitution at the P[double bond, length half m-dash]S centre of a benzylic phosphonamidothioic chloride

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Martin J. P. Harger

Abstract

The two diastereoisomers of ArCH2P(S)(NMeR*)Cl (Ar = 4-NO2C6H4, R* = CHMePh) react with Et2NH (0.2 mol dm–3) in CH2Cl2 to give mixtures of the diastereoisomers of ArCH2P(S)(NMeR*)NEt2 in practically the same ratio (54.5:45.5 or 53:47); such non-stereospecificity points to a thiophosphene intermediate ArCH[double bond, length half m-dash]P(S)NMeR* as the product-forming species.

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