Fluorinative Beckmann fragmentation: fluorinative alpha-cleavage of cyclic ketoximes by diethylaminosulfur trifluoride.
Diethylaminosulfur trifluoride reacted with cyclic ketoximes bearing substituent(s) that can stabilize a carbocation to cause fluorinative fragmentation, affording fluorinated carbonitrile. Ketoximes lacking such substituents afforded complex mixtures. However, the introduction of a sulfur functionality, which can stabilize a carbocation and can be easily removed from the reaction products, into the ketoxime was effective for producing the fluorinative fragmentation.
Kirihara
M
M
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Japan.
Niimi
K
K
Okumura
M
M
Momose
T
T
D004048:Diethylamines; D005461:Fluorine; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010091:Oximes / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
D004048:Diethylamines; D007202:Indicators and Reagents; D010091:Oximes; D005461:Fluorine; C040394:diethylaminosulfur trifluoride