The bromination reactions of isomeric 7,8-dibromobenzobicyclo[2.2.2]octa-2,5-dienes were studied and the possible role of neighbouring groups in rearrangements was investigated. Bromination of endo-cis dibromide 9 gives only the rearranged product 14 while the reaction of the exo-cis-dibromide 11 under the same conditions gives only non-rearranged products 15, 16 and 19. The possible role of substituents in the rearrangements was discussed.
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25.
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