Photochemical Preparation of 1,3,5,7-Tetracyanoadamantane and Its Conversion to 1,3,5,7-Tetrakis(aminomethyl)adamantane
journal contributionposted 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
Any type of content formally published in an academic journal, usually following a peer-review process.
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.