94193-63-2Relevant academic research and scientific papers
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.
