Collect. Czech. Chem. Commun. 1991, 56, 425-435

An account of regioselectivity in [2 + 3] cycloaddition of benzonitrile N-oxides with nitroethene by PMO theory

Andrzej Barańskia and Gyula Bánkib

a Institute of Organic Chemistry and Technology, Technical University, 31-155 Cracow, Poland
b Department of Organic Chemistry Slovak Institute of Technology, 880 37 Bratislava, Czechoslovakia


The application of PMO treatment to [2 + 3] cycloaddition of nitroethene to benzonitrile N-oxides is described. It was found that the reaction is under charge transfer control and PMO considerations based on MNDO calculations allow for the elucidation of the observed regioselectivity.