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Photochemical Preparation of 1,3,5,7-Tetracyanoadamantane and Its Conversion to 1,3,5,7-Tetrakis(aminomethyl)adamantane

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journal contribution
posted on 27.05.2004 by Ging S. Lee, Jude N. Bashara, Ghiwa Sabih, Asmik Oganesyan, Gayane Godjoian, Hieu M. Duong, Eric R. Marinez, Carlos G. Gutiérrez
New adamantane derivatives 1 and 2 that bear functionalized one-carbon extensions at all four bridgehead positions have been prepared. Radical nucleophilic substitution (SRN1) 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.