Lossen-like rearrangement of N-[α-methylbenzyl (phenyl) phosphinoyl]-O-methylsulfonylhydroxylamine with methylamine: retention of configuration at phosphorus as …

J Fawcett, MJP Harger, RS Menon

Index: Fawcett, John; Harger, Martin J. P.; Sreedharan-Menon, Ramesh Journal of the Chemical Society, Chemical Communications, 1992 , # 3 p. 227 - 229

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Abstract

N-Phosphinoylhydroxylamines are the phosphorus analogues of hydroxamic acids, and the 0-sulfonyl derivatives 1 (R = phenyl or alkyl) undergo a Lossen-like rearrangement with base (Scheme 1).1 This involves migration of a phenyl group from phosphorus to nitrogen, and gives rise to a phosphon- amide product such as 3. The monomeric metaphosphonimi- date 2 is a plausible intermediate, being analogous to the isocyanate formed in a Lossen ...