Understanding the participation of quadricyclane as nucleophile in polar [2sigma + 2sigma + 2pi] cycloadditions toward electrophilic pi molecules.

Abstract

The formal [2sigma + 2sigma + 2pi] cycloaddition of quadricyclane, 1, with dimethyl azodicarboxylate, 2, in water has been studied using DFT methods at the B3LYP/6-31G** and MPWB1K/6-31G** levels. In the gas phase, the reaction of 1 with 2 has a two-stage mechanism with a large polar character and an activation barrier of 23.2 kcal/mol. Inclusion of water… (More)
DOI: 10.1021/jo801575g

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