We recently reported long-range hyperconjugation in a constrained oxocane. In order to evaluate the potential for remote anchimeric assistance in such systems, steric factors must be ruled out. We report conformational analysis, spectroscopic properties, and natural bond orbital (NBO) analysis of 3+4 cycloadducts with and without heteroatom incorporation. These finding suggest that preorganization decreases the energy barrier toward nucleophilic substitution at a distal electrophilic site.

Evaluation of long-range hyperconjugation in constrained eight-membered rings

255th National Meeting (2018)

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