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.

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.