85357-60-4Relevant articles and documents
N-(Alkylphenylphosphinoyl)hydroxylamines: Highly Selective Migration of the Phenyl Group in the Base-induced Rearrangement of their O-Methylsulphonyl Derivatives
Harger, Martin J. P.,Smith, Adrian
, p. 683 - 688 (2007/10/02)
The N-(alkylphenylphosphinoyl)hydroxylamines RPh(O)NHOH (R=Me, Et, or Pri) have been prepared and converted into their O-methylsulphonyl derivatives RPhP(O)NHOMs.These readily rearrange on treatment with methylamine, t-butylamine, or sodium methoxide-methanol to give only the products RP(O)(NHPh)X (X=NHMe, NHBut, or OMe) resulting from migration of the phenyl group.The rates of reaction are essentially the same when R=Me and R=Pri, indicating that the rearrangement is not brought about by nucleophilic attack at phosphorus.A likely mechanism involves base-induced rearrangement to a monomeric metaphosphonimidate which then reacts rapidly with the nucleophile.
Base-induced Rearrangement of the O-Methanesulphonyl Derivatives of N-(Alkylphenylphosphinoyl)hydroxylamines. Highly Selective Migration of the Phenyl Group
Harger, Martin J. P.,Smith, Adrian
, p. 1140 - 1141 (2007/10/02)
The N-(alkylphenylphosphinoyl)-O-methanesulphonylhydroxylamines RPhP(O)NHOSO2Me (R = Me, Et, or Pri) react readily with MeNH2 or NaOMe-MeOH to give products resulting from phenyl, but not alkyl, migration.
The Proton Magnetic Resonance Spectra of Chiral Phosphinate Esters. Chemical Shift Non-equivalence of Enantiomers induced by Optically Active Phosphinothioic Acids
Harger, Martin J. P.
, p. 1505 - 1511 (2007/10/02)
The 1H n.m.r. spectrum of racemic methyl methylphenylphosphinate recorded in CCl4 solution in the presence of 1 mol. equiv. of (+)-(R)-phenyl-t-butylphosphinothioic acid or (-)-(S)-methylphenylphosphinothioic acid contains well separated P-m
