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Issue 2, 1999
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Base induced rearrangement reactions of N-phosphinoyl-O-sulfonylhydroxylamines. Observation of a phosphonamidic–sulfonic anhydride intermediate by NMR spectroscopy 1

Martin J. P. Harger  and  Ramesh Sreedharan-Menon 

Abstract

The hydroxylamine derivative PhRP(O)NHOSO2Me (R = PhMeCH) reacts with ButNH2 to give the rearrangement product RP(O)(NHPh)NHBut by way of a reactive but non-transient intermediate. At low amine concentrations the intermediate can be observed by 31P NMR spectroscopy; it is thought to be the mixed anhydride RP(O)(NHPh)OSO2Me as it has the same chemical shift as an authentic sample generated from RP(O)(NHPh)Cl and AgOSO2Me. The intermediate is formed with high (or complete) stereospecificity but it reacts with ButNH2 with low stereospecificity.

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Article type: Paper
DOI: 10.1039/A809267B
Citation: J. Chem. Soc., Perkin Trans. 2, 1999,0, 159-164
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    Base induced rearrangement reactions of N-phosphinoyl-O-sulfonylhydroxylamines. Observation of a phosphonamidic–sulfonic anhydride intermediate by NMR spectroscopy 1

    M. J. P. Harger and R. Sreedharan-Menon, J. Chem. Soc., Perkin Trans. 2, 1999, 0, 159
    DOI: 10.1039/A809267B

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