Use of an (18)O-labelled phosphonamidic-sulfonic anhydride to learn more about the mechanism by which O-sulfonyl-N-phosphinoylhydroxylamines rearrange

With Bu(t)NH2 the anhydride R(PhNH)P(O)OS(18)O2Bn 5 (R = Bu(t)), like the hydroxylamine derivative R(Ph)P(O)NHOS(18)O2Bn 4 (R = PhMeCH), gives Bu(t)NHS(18)O2Bn containing only a part (76-78%) of the available (18)O label; this is a result of partial scrambling of the label in 5 (OS(18)O2 (18)OSO2)...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2006-05, Vol.4 (10), p.1863-1864
Main Author: Harger, Martin J P
Format: Article
Language:English
Online Access:Get full text
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Summary:With Bu(t)NH2 the anhydride R(PhNH)P(O)OS(18)O2Bn 5 (R = Bu(t)), like the hydroxylamine derivative R(Ph)P(O)NHOS(18)O2Bn 4 (R = PhMeCH), gives Bu(t)NHS(18)O2Bn containing only a part (76-78%) of the available (18)O label; this is a result of partial scrambling of the label in 5 (OS(18)O2 (18)OSO2) while it is reacting; there is no need to postulate scrambling in the rearrangement of 4 to 5 (R = PhMeCH) or to exclude a concerted mechanism.
ISSN:1477-0520
DOI:10.1039/b603051c