Bridgehead reactivity in protoadamantane. Ionic bromination
Abstract
In agreement with computer molecular mechanics calculations, the preponderant product of bromination of protoadamantane (tricyclo[4.3.1.03,8]decane) is the 6-bromo-derivative. The structure elucidation is based on the finding that 6-methylprotoadamantane is significantly less reactive in bromination than is protoadamantane. 6-Bromoprotoadamantane reacts readily in several nucleophilic substitution reactions.