Electrolytic partial fluorination of organic compounds.: Part 27.: Regioselective anodic monofluorination of 2-substituted 1,3-dithiolanon-4-ones using Et4NF•4HF and Et3N•3HF

被引:22
作者
Fuchigami, T [1 ]
Narizuka, S
Konno, A
Momota, K
机构
[1] Tokyo Inst Technol, Dept Elect Chem, Midori Ku, Yokohama, Kanagawa 226, Japan
[2] Shizuoka Univ, Fac Engn, Hamamatsu, Shizuoka 432, Japan
[3] Morita Chem Ind Co Ltd, Dept Res & Dev, Yodogawa Ku, Osaka 532, Japan
关键词
anodic fluorination; 1,3-dithiolanone; regioselectivity; stereoselectivity; Et4NF center dot 4HF; Et3N center dot 3HF;
D O I
10.1016/S0013-4686(97)10122-0
中图分类号
O646 [电化学、电解、磁化学];
学科分类号
081704 ;
摘要
Highly regioselective anodic monofluorination of 2-substituted 1,3-dithiolan-4-ones was successfully carried out by using novel supporting electrolyte, Et4NF . 4HF while a conventional supporting electrolyte, Et3N . 3HF gave poor yields and/or low current efficiencies owing to severe passivation of the anode during the electrolysis. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1985 / 1989
页数:5
相关论文
共 26 条
[1]  
[Anonymous], 1991, Fluorine in Bioorganic Chemistry
[2]   ELECTROCHEMICAL MONOFLUORINATION OF PYRIDINE - SYNTHESIS OF 2-FLUOROPYRIDINE AT A PLATINUM ANODE [J].
BALLINGER, JR ;
TEARE, FW ;
BOWEN, BM ;
GARNETT, ES .
ELECTROCHIMICA ACTA, 1985, 30 (08) :1075-1077
[3]  
Childs W. V., 1991, ORGANIC ELECTROCHEMI
[4]  
Filler R., 1982, Biomedicinal Aspects of Fluorine Chemistry
[5]  
Fuchigami T, 1997, DENKI KAGAKU, V65, P626
[6]   Highly selective electrochemical fluorination of organic compounds [J].
Fuchigami, T ;
Konno, A .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1997, 55 (04) :301-312
[7]  
FUCHIGAMI T, 1994, REV HETEROATOM CHEM, V10, P155
[8]  
FUCHIGAMI T, 1992, J ORG CHEM, V57, P6074
[9]  
FUCHIGAMI T, UNPUB
[10]   ELECTROCHEMICAL PRODUCTION OF PARTIALLY FLUORINATED ORGANIC-COMPOUNDS - N-METHYLMORPHOLINE FLUORINATION [J].
GAMBARETTO, GP ;
NAPOLI, M ;
FRACCARO, C ;
CONTE, L .
JOURNAL OF FLUORINE CHEMISTRY, 1982, 19 (3-6) :427-436