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.
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