title: Photochemical preparation of 1,3,5,7-tetracyanoadamantane and its conversion to 1,3,5,7-tetrakis(aminomethyl)adamantane.
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]
authors.affiliation: Department of Chemistry and Biochemistry, California State University, Los Angeles, CA 90032-8202, USA.
authors.forename: Ging S
authors.initials: GS
authors.lastname: Lee
authors.forename: Jude N
authors.initials: JN
authors.lastname: Bashara
authors.forename: Ghiwa
authors.initials: G
authors.lastname: Sabih
authors.forename: Asmik
authors.initials: A
authors.lastname: Oganesyan
authors.forename: Gayane
authors.initials: G
authors.lastname: Godjoian
authors.forename: Hieu M
authors.initials: HM
authors.lastname: Duong
authors.forename: Eric R
authors.initials: ER
authors.lastname: Marinez
authors.forename: Carlos G
authors.initials: CG
authors.lastname: Gutiérrez
mesh_terms: D000218:Adamantane / Q000031:analogs & derivatives / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010777:Photochemistry
chemical_list: C489018:1,3,5,7-tetracyanoadamantane; C489020:1,3,5,7-tetrakis(aminomethyl)adamantane; D000218:Adamantane