105584-85-8Relevant academic research and scientific papers
O-Sulphonyl-N-phosphoylhydroxylamines: Nucleophilic Attack at Nitrogen by Dimethyl Sulphide and Allyl Methyl Sulphide Leading to N-Phosphoyl Sulphilimines
Harger, Martin J. P.,Smith, Adrian
, p. 377 - 380 (2007/10/02)
The O-sulphonyl-N-phosphoylhydroxylamines RR'P(O)NHX 6H4O; X=OMs or ONs> generally react with dimethyl sulphide and allyl methyl sulphide at room temperature in the absence of base.Nucleophilic attack at nitrogen, with displacement of the sulphonate anion, gives the protonated N-phosphoyl sulphilimines which is converted into the free sulphilimine on treatment with base.The allylic sulphilimines are labile, undergoing -sigmatropic rearrangement to N-phosphoyl-N-allylsulphenamides .In the light of these results, the formation of some sulphilimine when the base-induced rearrangement of Ph2P(O)NHOMs is carried out in dimethyl sulphide need not be seen as evidence for a nitrene mechanism.
