56875-30-0Relevant academic research and scientific papers
A Convenient Synthetic Route to N-Aryl and N-Alkylamino(alkyl) Phosphonates and Phosphine Oxides
Couture, A.,Deniau, E.,Woisel, P.,Grandclaudon, P.
, p. 2483 - 2486 (2007/10/02)
A variety of phosphorylated N-aryl and N-alkyl N-formyl and N-tert-butoxycarbonylaminomethyl derivatives have been efficiently prepared by treatment of the corresponding chloromethyl derivatives with a trialkyl phosphite or an alkyl diphenylphosphinite.These bifunctional compounds may be deprotonated with LDA and further submitted to electrophilic substitution.An acidic treatment of the resulting compounds gives rise to a range of N-aryl and N-alkylamino(alkyl) phosphonates and phosphine oxides.
Reactions of N-Phenyl α-Halogenophosphonamidates with Alkoxide: Migration of the Anilino Group from Phosphorus to the α Carbon Atom
Harger, Martin J. P.,Williams, Andrew
, p. 1681 - 1686 (2007/10/02)
When Me2CClP(O)(NHPh)OMe is treated with 0.5M NaOMe-MeOH the anilino group migrates from phosphorus to the α carbon atom.Reaction is complete within 2 min at 60 deg C and Me2C(NHPh)P(O)(OMe)2 is formed quantitatively.Similar behaviour is observed with MeCHClP(O)(NHPh)OMe but the reaction is ca. 50-times slower and in the later stages some of the resulting MeCH(NHPh)P(O)(OMe)2 becomes demethylated.For the still less reactive compounds XCH2P(O)(NHPh)OMe (X = Cl or I) demethylation of the substrate and/or product is extensive, but with ICH2P(O)(NHPh)OEt in 0.15M NaOEt-EtOH at 60 deg C the product PhNHCH2P(O)(OEt)2 can be obtained within 1 h in high yield.The relative rates of rearrangement of the various substrates are consistent with a mechanism involving a three-membered cyclic intermediate, the phosphorus analogue of an α-lactam.
