Regioselectivity in the reaction of azinium salts and ylides with tetracyanoethylene

  • A. M. Shestopalov
  • I. A. Aitov
  • Yu. A. Sharanin
  • V. P. Litvinov
Organic Chemistry


The reactions of pyridinium, picolinium, and quinolinium salts and ylides with tetracyanoethylene have been found to be regioselective. Reaction of azinium salts with tetracyanoethylene in aqueous methanol affords azinium tricyanoethylenolates, but pyridinium ylides react differently, with the highly stereo-selective formation of the Z-isomers of 3-aroyl-3-(R-1-pyridinio)-1,1,2-tricyano-2-propen-1-ides, which are 1,4-ylides with maximum charge separation.


Methanol Pyridinium Quinolinium Charge Separation Aqueous Methanol 
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Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • A. M. Shestopalov
    • 1
  • I. A. Aitov
    • 1
  • Yu. A. Sharanin
    • 1
  • V. P. Litvinov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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