Direct Clay-Catalyzed Friedel-Crafts Arylation and Chlorination of the Hydrocarbon Adamantane

Multiple chlorinations and arylations at the tertiary positions of adamantane are promoted by FeCl₃-doped K10 montmorillonite in CCl₄ or in aromatic solvents. The process, remarkably easy to implement, can be tailored to selective formation of monosubstituted 1-adamantyl derivatives or 1,3-disubstituted adamantanes. The process achieves alkylation at the meta- and para-positions of toluene leading to a purely statistical distribution and displays no substrate specificity in competition experiments between toluene and benzene.