Quantum-chemical study of the mechanism and regioselectivity of transannular cyclization of dienes of the bicyclo[3.3]nonane series treated with bromosuccinimide and F=TEDA-BF_4

摘要

We have shown that, in transannular cyclization of 3,7-bismethylenebicyclo[3.3]nonane derivatives with methyl or phenyl substitents in one of the exocyclic methylene groups, when N-bromosuccinimide is used the bromine atom is added tot eh unsubstituted double bond; and when the electrophilic fluorinating reagent F-TEDA-BF_4 is used, the bromine atom is added to the substituted double bond. We have used the PM3 semiempirical method to stdy the mechanism of these reactions.