153908-60-2Relevant academic research and scientific papers
N-(diphenylphosphinothioyl)hydroxylamine: Preparation, characterisation and base-induced transposition of sulfur and oxygen atoms in its O-benzoyl derivative
Harger, Martin J. P.
, p. 3205 - 3209 (2007/10/03)
N-(Diphenylphosphinothioyl)hydroxylamine 5 has been prepared from Ph2P(S)Cl using H2NOSiMe3 and has been converted into its O-benzoyl derivative Ph2P(S)NHOCOPh 6. The principal reaction of the derivative 6 with base (NaOMe or ButNH2) is rearrangement, transposition of sulfur and oxygen giving Ph2P(O)NHSCOPh 7; this then reacts further, forming the phosphinic amide Ph2P(O)NH2 together with PhCO2Me or PhCONHBut. The rearrangement probably involves intramolecular nucleophilic displacement of benzoate by the P=S group of 6, forming an intermediate with P, N and S atoms in a three-membered ring.
