Abstract
The interaction of substituted trans-1,1-dicyano-4-phenyl-1,3-butadienes with pyridinium ylides proceeds through the path of [π4s+π2s]-dipolar cycloaddition, highly regioselective and stereoselective, with the formation of substituted 1-(2,2-dicyanovinyl)-2-phenyl-6-cyano-1,2-trans-2,3-trans-1,9-trans-1,2,3,9-tetrahydroindolizines. The stereoselectivity of these reactions is due to endo-addition of molecules of trans-1,3-butadienes to the anti form of the pyridinium ylides; it is confirmed by correlation analysis of the data from double PMR, mathematical calculations of torsion angles, and x-ray structural studies of the substituted tetrahydroindolizines.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1354–1360, October, 1991.
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Shestopalov, A.M., Sharanin, Y.A., Nesterov, V.N. et al. Stereoselective [π4s+π2s]-dipolar cycloaddition of pyridinium ylides to nitriles of the trans-1,3-butadiene series. Crystal and molecular structure of 3-benzoyl-1-(2,2-dicyano-1-cyclopropylvinyl)-2-phenyl-6-cyano-1,2-trans-2,3-trans-1,9-trans-1,2,3,9-tetrahydroindolizine. Chem Heterocycl Compd 27, 1084–1090 (1991). https://doi.org/10.1007/BF00486803
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DOI: https://doi.org/10.1007/BF00486803