Abstract
1,1,2,2-Tetracyanocyclobutanes are most frequently synthesized by a [2+2]-cycloaddition reaction [134]. The most facile reaction occurs between tetracyanoethylene and alkenes whose double bond is activated by electron-donor substituents. 1,1,2,2-tetracyanocyclobutanes are considered to be formed by a nonconcerted cycloaddition reaction involving a zwitterionic intermediate. The reactions of tetracyanoethylene with styrene [5] and vinyl ether [6] are assigned to this type of reactions. It is shown that first a charge-transfer complex is formed. Further, say, in the reaction of tetracyanoethylene with styrene, the
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