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Issue 17, 2004
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Phosphoramidic acid monoesters as phosphorylating agents: steric effects and reluctance to form monomeric metaphosphate intermediates

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Abstract

The formation of phosphate diesters (RO)2P(X)OH (R = Et, Pri or Pri2CH) by phosphorylation of ROH with ROP(X)(NPri2)OH is insensitive to steric effects when X = S but not when X = O; this is consistent with a unimolecular mechanism and a thiometaphosphate (ROPOS) intermediate when X = S but a bimolecular SN2(P) mechanism when X = O.

Graphical abstract: Phosphoramidic acid monoesters as phosphorylating agents: steric effects and reluctance to form monomeric metaphosphate intermediates

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Article information


Submitted
10 May 2004
Accepted
18 Jun 2004
First published
28 Jul 2004

Chem. Commun., 2004, 1952-1953
Article type
Communication

Phosphoramidic acid monoesters as phosphorylating agents: steric effects and reluctance to form monomeric metaphosphate intermediates

M. J. P. Harger, Chem. Commun., 2004, 1952
DOI: 10.1039/B406896C

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