Photochemical preparation of 1,3,5,7-tetracyanoadamantane and its conversion to 1,3,5,7-tetrakis(aminomethyl)adamantane.

New adamantane derivatives 1 and 2 that bear functionalized one-carbon extensions at all four bridgehead positions have been prepared. Radical nucleophilic substitution (S(RN)1) reaction of 1,3,5,7-tetrabromoadamantane with cyanide produces 1,3,5,7-tetracyanoadamantane (1), which was reduced with borane reagents to 1,3,5,7-tetrakis(aminomethyl)adamantane (2). Improvements in the preparation of 1,3,5,7-tetrahaloadamantanes (halogen = Br, Cl, I) are also reported. [structure--see text]