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Stereoselectivity, Non-stereospecificity, and the Lifetime of the Thiometaphosphonimidate Intermediate formed in the Reactions of the Diastereoisomers of a Phosphonamidothioic Chloride with t-Butylamine

DOI: 10.1039/c39880001256

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 1256 - 1257 (1988)

Update date:2022-08-03

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Authors:

Harger, Martin J. P.Harger, Martin J. P.

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Article abstract of DOI:10.1039/c39880001256

Both diastereoisomers of t-BuP(S)(Cl)NHR react with t-BuNH2 (0.25 M) in an aprotic solvent to give the same mixture of the diastereoisomers of t-BuP(S)(NHt-Bu)NHR (no stereospecificity), but the diastereoisomer ratio of the product (stereoselectivity) increases from 57 : 43 (MeCN) to 80 : 20 (cyclohexane) as the polarity (ετ) of the solvent is reduced.

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Product name:N-<(S)-α-phenylethyl>-P-t-butylphosphonamidothioic acid

Cas No:122183-07-7

122183-07-7

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