Photochemical preparation of 1,3,5,7-tetracyanoadamantane and its conversion to 1,3,5,7-tetrakis(aminomethyl)adamantane.
| Autor: | Lee GS; Department of Chemistry and Biochemistry, California State University, Los Angeles, CA 90032-8202, USA., Bashara JN, Sabih G, Oganesyan A, Godjoian G, Duong HM, Marinez ER, Gutiérrez CG |
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| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2004 May 27; Vol. 6 (11), pp. 1705-7. |
| DOI: | 10.1021/ol036526g |
| Abstrakt: | 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] |
| Databáze: | MEDLINE |
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