Bromination of 2,3-Dibromobenzobarrelene at Different Conditions: Highly Brominated Benzobicyclic Systems


Abstract: The electrophilic addition of bromine to 2,3-dibromobenzobarrelene at 10^oC led to the formation of completely rearranged products in high yield. Bromination of 2,3-dibromobenzobarrelene with molecular bromine in decalin at 150^oC and with DBTCE in CCl_{4} at 77^oC gave rearranged and non-rearranged products. The radical and ionic mechanism are discussed. All compounds were characterized properly, by NMR spectroscopy and chemical transformation.

Keywords: benzobarrelene, high temperature bromination, Wagner-Meerwein rearrangement and poly-bromides.

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