Photochemical preparation of 1,3,5,7-tetracyanoadamantane and its conversion to 1,3,5,7-tetrakis(aminomethyl)adamantane |
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| Authors: | Lee Ging S Bashara Jude N Sabih Ghiwa Oganesyan Asmik Godjoian Gayane Duong Hieu M Marinez Eric R Gutiérrez Carlos G |
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| Affiliation: | Department of Chemistry and Biochemistry, California State University, Los Angeles, CA 90032-8202, USA. |
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| Abstract: | 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] |
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