Tetrahedron

N-(dialkylphosphinoyl) hydroxylamines: Preparation using N, O-bis (trimethylsilyl) hydroxylamine and migration of simple alkyl groups in the rearrangements of their …

MJP Harger, PA Shimmin

Index: Harger, Martin J. P.; Shimmin, P. Andrew Tetrahedron, 1992 , vol. 48, # 36 p. 7539 - 7550

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Citation Number: 17

Abstract

Treatment of Pri2P (O) Cl with Me3SiNHOSiMe3 gives Pri2P (O) NHOSiMe3, which is desilylated by methanol giving Pri2P (O) NHOH. The Op-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 ...