76429-91-9Relevant articles and documents
Formation of (1-adamantylcarbinyl)arenes from 3-azidohomoadamantane-aluminum chloride-aromatic substrates
Margosian, Daniel,Speier, Jon,Kovacic, Peter
, p. 1346 - 1350 (1981)
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 kT/kB 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.