N-phosphonoyl and N-phosphoroyl hydroxylamines: reactions of their O-sulphonyl derivatives with t-butylamine

Abstract

The N-phosphonoylhydroxylamines Ph(ArO)P(O)NHOH (Ar =p-chlorophenyl or p-tolyl) and the N-phosphoroylhydroxylamines (ArO)₂P(O)NHOH (Ar =p-chlorophenyl or p-tolyl) have been prepared and converted into their O-methanesulphonyl and O-p-nitrobenzenesulphonyl derivatives. In the reactions of the sulphonyl derivatives with t-butylamine, the phosphonoyl compounds undergo a Lossen-like rearrangement with migration of the phenyl group from phosphorus to nitrogen. The phosphoroyl compounds do not rearrange with t-butylamine but give products that include (ArO)₂P(O)NH₂and (ArO)₂P(O)NHNHBu^t.