18856-91-2Relevant academic research and scientific papers
Synthesis of N-diphenylphosphinoylimines using the Kresze reaction
Lauzon, Caroline,Desrosiers, Jean-Nicolas,Charette, Andre B.
, p. 10579 - 10580 (2007/10/03)
The synthesis of N-diphenylphosphinoylimines involving the treatment of aldehydes with P,P-diphenyl N-sulfmylphosphoramidate (Ph2P(O)NSO) is described. The reagent is prepared from P,P-diphenylphosphinic amide, thionyl chloride, and imidazole.
Reactivity and diastereoselectivity in the thermal and Lewis acid- catalyzed Diels-Alder reactions of N-sulfinylphosphoramidates
Zhang,Flann
, p. 1372 - 1378 (2007/10/03)
The [4 + 2] cycloaddition reactions of N-sulfinylphosphoromidates, prepared from the corresponding phosphoramidates by treatment with N- (chlorosulfinyl)imidazole, and 1,3-cyclohexadiene were found to be diastereoselective in the absence (>90:10) and presence (> 95:5) of Lewis acid. The sulfur configuration of the major adduct from the cycloaddition reaction has been established unambiguously by X-ray crystallography. The use of Lewis acids improved the diastereoselectivity and yield, as Well as shortened reaction times. Based on the intermediacy of a tin chelate, and the absence of phosphoryl secondary orbital interactions, a mechanism for the cycloaddition reactions is discussed.
