654674-48-3Relevant academic research and scientific papers
A new concept for the efficient synthesis of chiral phosphorus-nitrogen-carbon cage compounds
Hoffmann, Nils,Wismach, Catleen,Ernst, Ludger,Schiebel, Hans-Martin,Jones, Peter G.,Streubel, Rainer
, p. 1815 - 1821 (2007/10/03)
A new concept for the efficient synthesis of a chiral phosphorus-nitrogen-carbon cage-compound is reported, which is comprised of a high-yield three-step procedure starting from a P-Cp*-substituted 2H-azaphosphirene complex. Thermolysis of a solution of the latter complex in the presence of Ph3PNCN and DMAD afforded the P-Cp*-substituted 2H1,2-azaphosphole complex 11 in a clean reaction; a further reaction at 75 °C with DMAD produced complex 12 via an intermolecular Diels-Alder reaction of the Cp* group. A subsequent intramolecular Diels-Alder reaction of 12, at 120 °C, yielded the title compound, complex 13, in quantitative yields. Elemental analyses and detailed (solution) NMR spectroscopic and MS investigations confirmed all complexes. Furthermore, solid state structures of complexes 11 and 13 were established by X-ray single crystal structure analyses. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
