84718-88-7Relevant 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.
Photolysis of Diphenyl- and t-Butyl(phenyl)-phosphinic Azides: Dimethyl Sulphide as a Nitrene Trap, and Its Influence on the Curtius-like Rearrangement
Harger, Martin J.P.,Westlake, Sally
, p. 2351 - 2356 (2007/10/02)
Photolysis of Ph2P(O)N3 in benzene containing MeOH gives a high yield (72percent) of the phosphonamidate PhP(O)(OMe)NHPh (3) resulting from Curtius-like rearrangement.When some of the benzene solvent is replaced by Me2S the yield of the rearrangement prod
DIMETHYLSULPHIDE AS A NITRENE TRAP IN THE PHOTOLYSIS OF SOME PHOSPHINIC AZIDES
Harger, Martin J. P.,Westlake, Sally
, p. 3621 - 3622 (2007/10/02)
When PhRP(O)N3 (R=Ph or t-Bu) is photolysed in dimethylsulphide substantial amounts (22-32percent) of PhRP(O)N:SMe2 and PhRP(O)NHCH2SMe are produced and rearrangement is less important than in benzene.
