51028-18-3Relevant academic research and scientific papers
Stereoselective addition of grignard reagents to new P-chirogenic N-phosphinoylbenzaldimines: Effect of the phosphorus substituents on the stereoselectivity
Notar Francesco, Irene,Egloff, Coraline,Wagner, Alain,Colobert, Francoise
scheme or table, p. 4037 - 4045 (2011/09/15)
Several phosphinoylimines have been synthesized in five steps by starting from the appropriate phosphane oxide and were then treated with methylmagnesium bromide to give both diastereoisomers in high yields and with promising diastereomeric ratios. Then N-[(tert-butyl)(phenyl)phosphinoyl]benzaldimine, which displayed the best results, was subjected to the 1,2-addition of various Grignard reagents to evaluate the best chiral induction due to the stereogenic phosphorus atom. The corresponding adducts were obtained in excellent yields and with moderate to excellent diastereoisomeric ratios. Copyright
Stereoselective addition of Grignard reagents to new P-chirogenic N-phosphinoylimines
Francesco, Irene Notar,Wagner, Alain,Colobert, Francoise
supporting information; experimental part, p. 2139 - 2141 (2010/07/04)
The addition of various Grignard reagents to P-t-butyl-P-phenyl-N- phosphinoyl benzaldimine provides a stereoselective method for the synthesis of chiral phosphinoylamines. The Royal Society of Chemistry.
One-step transformation of ammonium dialkyl phosphoroselenoates into dialkyl phosphoramidates
Mielniczak, Grazyna,Lopusinski, Andrzej
, p. 121 - 127 (2007/10/03)
Ammonium dialkyl phosphoroselenoates are directly converted into the dialkyl phosphoramidates by iodosobenzene and iodoxybenzene. The inversion of configuration at the phosphorus atom, using model diastereoisomeric ammonium cis- and trans-2-oxo-2-seleno-4-methyl-1,3,2-dioxaphosphinan system, was observed. The mechanistic scheme of this transformation is discussed.
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.
PHOTOLYSIS OF SOME UNSYMMETRICAL PHOSPHINIC AZIDES IN METHANOL. RELATIVE MIGRATORY APTITUDES OF ALKYL GROUPS AND PHENYL IN THE CURTIUS-LIKE REARRANGEMENT.
Harger, Martin J. P.,Westlake, Sally
, p. 3073 - 3078 (2007/10/02)
When an alkylphenylphosphinic azide RPhP(O)N3 (R=Me, Et, Pri or But) is photolysed in MeOH either the alkyl or phenyl group can migrate from P to N in the Curtius-like rearrangement.The composition of the product shows that migration of the alkyl group R is preferred.However, the preference is not great and decreases as R changes But->Pri->Et->Me-> (approx. migratory aptitudes relative to Ph: 2.1, 1.7, 1.3, 1.2 respectively), probably because the Ph-P bond is better able to assume the correct conformation for Ph migration when R is less bulky.For t-butylmethylphosphinic azide there is very little preference for migration of But relative to Me.Small amounts of unrearranged products such as ButPhP(O)NHOMe and ButPhP(O)NH2 are generally produced in the photolyses, together with the methyl phosphinates RPhP(O)OMe (major product when R=Me) resulting from (non-photochemical) solvolysis of the azide.
