Formation of (1-adamantylcarbinyl)arenes from 3-azidohomoadamantane-aluminum chloride-aromatic substrates

Article abstract of DOI:10.1021/jo00320a023

Reaction of 3-azidohomoadamantane with aromatic substrates catalyzed by aluminum chloride at 80 °C gave the corresponding (1-adamantylcarbinyl)arene in >90% yield. The reaction proceeds exclusively with elimination of azide ion. Competitive reaction with toluene (T)-benzene (B) gave an average k_T/k_B of ～14/1. The results indicate that a straightforward primary cation is probably not the actual attacking electrophile. The possible intervention of a bridged ion is discussed.