Abstract
Bromination of exo- and endo-tricyclo[3.2.1.0 2,4]oct-6-ene is initiated at the double bond. This is in contrast to reaction with acid where reaction is initiated preferentially at the cyclopropane. The stationary points on the potential energy surfaces that result from bromine addition to the double bond have been identified by semi-empirical methods. The non-classical bromonium ions are predicted to be less stable than the classical structures. The exo-cyclopropylalkene gives cis and trans 1,2-dibromides along with products which result from reaction of bromine at the exo face of the alkene with subsequent rearrangement involving the C2C4 or C2C3 cyclopropyl bonds. The endo-cyclopropylalkene similarly reacts with bromine at the exo face of the alkene, but 1,2-addition does not compete with rearrangement.
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