Quantum-Chemical Study of the Mechanism and Regioselectivity of Transannular Cyclization of Dienes of the Bicyclo[3.3.1]nonane Series Treated with Bromosuccinimide and F-TEDA-BF 4

Abstract

We have shown that, in transannular cyclization of 3,7-bismethylenebicyclo[3.3.1]nonane derivatives with methyl or phenyl substituents in one of the exocyclic methylene groups, when N-bromosuccinimide is used the bromine atom is added to the unsubstituted double bond; and when the electrophilic fluorinating reagent F-TEDA-BF4 is used, the bromine atom is added to the substituted double bond. We have used the PM3 semiempirical method to study the mechanism of these reactions.