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