Selective fluorination of adamantanes by an electrochemical method.
Selective fluorination of adamantanes was achieved by the electrochemical fluorination method, using Et 3N-5HF as electrolyte and a fluorine source. Mono-, di-, tri-, and tetrafluoroadamantanes were selectively prepared from adamantanes by controlling the oxidation potential, and the fluorine atoms were introduced selectively at the tertiary carbons. Adamantanes that have functional groups such as ester, cyano, and acetoxymethyl were also fluorinated selectively.
Aoyama
Motoshi
M
Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan.
Fukuhara
Tsuyoshi
T
Hara
Shoji
S
D000218:Adamantane / Q000737:chemistry*; D004563:Electrochemistry / Q000379:methods*; D005461:Fluorine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
D005461:Fluorine; D000218:Adamantane