During 1,3 dipolar reactions of unsymmetrical mesoionic M�nchnones (1) to substituted nitrostyrenes (2), bicyclic intermediates (3) are formed, which then decompose to two observed products (4, 5), the ratio of which is contrary to what would be expected based on known electrostatics. As part of a larger study of this set of reactions, a computational study of possible transition states, both to and from the intermediate, was conducted in order to clarify the mechanism by which this reaction occurs, and shed light on the unexpected ratio of products.

Computational studies of transition states in bicyclic intermediates

245th National Meeting (2013)

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