94193-59-6Relevant 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.