- Electrolytic Partial Fluorination of Organic Compounds. 12. Selective Anodic Monofluorination of Fluoroalkyl and Alkyl Sulfides
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Highly regioselective anodic monofluorination of various aryl and alkyl fluoroalkyl sulfides was successfully carried out, and fluorine was exclusively (aryl sulfides) or preferentially (alkyl sulfides) introduced at the position α to the fluoroalkyl group.Even simple alkyl phenyl sulfides devoid of an electron-withdrawing group could be anodically monofluorinated in satisfactory yields for the first time when etheral solvents were used as an electrolytic solution.A unique Pummerer-type mechanism via fluorosulfonium ions was proposed for this anodic fluorination by comparison with anodic α-methoxylation previously studied.
- Fuchigami, Toshio,Konno, Akinori,Nakagawa, Kiyono,Shimojo, Moriyasu
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p. 5937 - 5941
(2007/10/02)
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- Electrolytic Partial Fluorination of Organic Compounds. Regioselective Anodic Monofluorination of Organosulfur Compounds
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Regioselective anodic monofluorination of aryl 2,2,2-trifluoroethyl sulfides gave, exclusively, aryl 1,2,2,2-tetrafluoroethyl sulfides, the products of fluorination at the position α to the trifluoromethyl group.The α-monofluorination of sulfides bearing
- Fuchigami, Toshio,Shimojo, Moriyasu,Konno, Akinori,Nakagawa, Kiyono
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p. 6074 - 6075
(2007/10/02)
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