During the 1,3-dipolar reaction of an unsymmetrical mesoionic M�nchnone (1) with �-nitrostyrene (2), bicyclic intermediates (3) are formed. These intermediates decompose to two observed products (4, 5), the ratio of which is contrary to what would be expected based on electrostatics. As part of a larger study of this reaction, a detailed computational study of the reaction energetics and transition state, from the starting materials (1, 2) through the intermediate structure (3), was conducted in order to elucidate the mechanism behind the unexpected regiochemistry.

Computational study of the energetics governing the regiochemistry of a 1,3-dipolar cycloaddition reaction

247th National Meeting (2014)

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