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