61017-18-3Relevant academic research and scientific papers
Preparation and Characterisation of N-(Diphenylphosphinoyl)hydroxylamine, and Conversion into O-Sulphonyl Derivatives that undergo Lossen-like Rearrangement
Harger, Martin J. P.
, p. 2699 - 2704 (2007/10/02)
Having previously shown that diphenylphosphinic chloride (1a) forms O-(diphenylphosphinoyl)hydroxylamine (3a) with hydroxylamine, we have now established that N-(diphenylphosphinoyl)hydroxylamine (2a) can be obtained in good yield by reaction of (1a) with O-trimethylsilylhydroxylamine followed by methanolytic removal of the silyl blocking group.The di-p-tolyl (2b) and bis-p-methoxyphenyl (2c) analogues can be prepared in a similar way.N-(Diphenylphosphinoyl)hydroxylamine is acetylated at the O atom with acetic anhydride, and is sulphonylated at O with methanesulphonyl chloride and toluene-p-sulphonyl chloride.The N-(diphenylphosphinoyl)-O-sulphonylhydroxylamines (8) and (12a) undergo rapid and quantitative Lossen-like rearrangement with methanol-sodium methoxide to give methyl N,P-diphenylphosphonamidate (11).Comparable rearrangement are observed with t-butylamine, aniline-triethylamine, and phenol-triethylamine.
