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B3LYP/6-31++G(d) calculations indicated that the reaction of (2 E )-3-phenyl-2-nitroprop-2-enenitrile with cyclopentadiene catalyzed by cations of 1,3-dialkylimidazolium ionic liquid shall not take place according to the classical scheme of one-step [2+4] Diels-Alder cycloaddition. Along the path finally leading to bicyclo[2.2.1]hept-5-ene (norbornene) with a nitro group in endo orientation, the process of bicarbocyclic skeleton formation shall take place according to the domino mechanism, via [2+4] heterocycloadduct. On the other hand, along the path leading finally to bicyclo[2.2.1]hept-5-ene with a nitro group in exo orientation, acyclic adduct with a zwitterionic nature is formed in the first reaction, which undergoes cyclisation next in the second step of the reaction.

monatshefte für chemie

First example of stepwise, zwitterionic mechanism for bicyclo[2.2.1]hept-5-ene (norbornene) formation process catalyzed by the 1-butyl-3-methylimidazolium cations