138123-12-3Relevant academic research and scientific papers
N-(Dialkylphosphinoyl)hydroxylamines : Preparation using N,O-Bis(trimethylsilyl)hydroxylamine and Migration of Simple Alkyl Groups in the Rearrangements of their O-p-Nitrobenzenesulphonates
Harger, Martin J. P.,Shimmin, P. Andrew
, p. 7539 - 7550 (1992)
Treatment of Pri2P(O)Cl with Me3SiNHOSiMe3 gives Pri2P(O)NHOSiMe3, which is desilylated by methanol giving Pri2P(O)NHOH.The O-p-nitrobenzenesulphonyl derivative of this rearranges with KOBut in ButOH, an isopropyl group migrating from P to N and the phosphonamidate PriP(O)(OBut)NHPri being formed quantitatively.Rearrangement also occurs in other alcohols (MeOH, EtOH, PriOH), but not quite as cleanly.In ButNH2 the phosphinoylhydrazine Pri2P(O)NHNHBut is formed as well as the rearrangement product, PriP(O)(NHBut)NHPri.The p-nitrobenzenesulphonyl derivatives of Et2P(O)NHOH and PriMeP(O)NHOH, prepared similarly with Me3SiNHOSiMe3, also rearrange quantitatively with ButOH - KOBut.In the latter case, the migratory aptitudes of the two alkyl groups (Pri and Me) are almost identical.
Preparation of Simple N-(Dialkylphosphinoyl)hydroxylamines and Alkyl Migration in the Rearrangement of their O-p-Nitrobenzenesulphonates
Harger, Martin J. P.,Shimmin, P. Andrew
, p. 4769 - 4770 (2007/10/02)
N-Phosphinoylhydroxylamines containing only simple alkyl groups (Me, Et, Pri) can be prepared using Me3SiNHOSiMe3; alkyl groups migrate from P to N when the derived O-p-nitrobenzenesulphonates react with base. Key words: N-Phosphinoylhydroxylam
