Abstract
The electrophilic addition of bromine to 13-anti-bromo-endo-benzocyclobutenonorbornene 7 at −50 ± 5 °C has led in high yield to the formation of the rearranged dibromides 9, 10 and 11. In addition to this, bromination of exo isomer 8 results in formation of rearranged 9 and non rearranged product 10. However, high-temperature bromination of endo 7 and exo isomer 8 at 77 °C gave only non-rearranged products. The possible role of a substituent in rearrangements is discussed in these systems.
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