Bromination of benzonorbornadiene (1) with sodium bromide in the presence of sodium perborate at room temperature gave only one product, the dibromide 2 produced via Wagner-Meerwein rearrangement. However, at high temperatures, bromination resulted predominantly in the formation of rearranged solvolytic products whose formation mechanisms are discussed.
ŞENOCAK, ERDAL; TAŞKESENLİGİL, YAVUZ; and TÜMER, FERHAN (2002) "Bromination of Benzonorbornadiene Using a Mixture of Sodium Bromide and Sodium Perborate at High Temperatures," Turkish Journal of Chemistry: Vol. 26: No. 6, Article 15. Available at: https://journals.tubitak.gov.tr/chem/vol26/iss6/15