Chemical Transformations of Tetracyclo[3.3.1.13,7.01,3]decane (1,3-Dehydroadamantane): IX. Noncatalytic Reactions with Alkylarenes

The reaction of 1,3-dehydroadamantane with alkylbenzenes was studied for the first time. It involved the C–H bond of the alkyl substituent in the α-position with respect to the aromatic ring. The proposed radical mechanism of the reaction was confirmed by the isolation of 1,1′-biadamantane and 1,2-diphenylethane derivatives. Difficultly accessible (adamantan-1-ylmethyl)arenes were synthesized in 53–78% yields.