Chemistry of Heterocyclic Compounds p. 1084 - 1090 (1991)
Update date:2022-09-26
Topics:
Shestopalov, A. M.
Sharanin, Yu. A.
Nesterov, V. N.
Khoroshilov, G. E.
Shklover, V. E.
et al.
The interaction of substituted trans-1,1-dicyano-4-phenyl-1,3-butadienes with pyridinium ylides proceeds through the path of s + ?2s>-dipolar cycloaddition, highly regioselective and stereoselective, with 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 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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