Electroorganic reaction in ionic liquids. Part 1: Electrolytic partial fluorination of organic compounds. Part 58. Electroorganic synthesis under solvent-free conditions. Highly regioselective anodic monofluorination of cyclic ethers, lactones, and a cyclic carbonate

被引:52
作者
Hasegawa, M [1 ]
Ishii, H [1 ]
Fuchigami, T [1 ]
机构
[1] Tokyo Inst Technol, Dept Elect Chem, Midori Ku, Yokohama, Kanagawa 2268502, Japan
关键词
D O I
10.1016/S0040-4039(02)00047-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Regioselective anodic fluorination of cyclic ethers, lactones, and a cyclic carbonate in Et4NF.nHF (n = 4, 5) and Et3N.5HF without a solvent was successfully carried out to give the corresponding monofluorinated products in moderate yields. This is the first report of direct electochemical fluorination of cyclic ethers, lactones, and a cyclic carbonate using anodic fluorination. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1503 / 1505
页数:3
相关论文
共 10 条
[1]   SYNTHESIS OF FLUORINATED ETHERS PERFLUOROGLYME AND PERFLUORODIGLYME BY DIRECT FLUORINATION [J].
ADCOCK, JL ;
LAGOW, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (20) :3617-3618
[2]   STM study on graphite/electrolyte interface in lithium-ion batteries: solid electrolyte interface formation in trifluoropropylene carbonate solution [J].
Inaba, M ;
Kawatate, Y ;
Funabiki, A ;
Jeong, SK ;
Abe, T ;
Ogumi, Z .
ELECTROCHIMICA ACTA, 1999, 45 (1-2) :99-105
[3]   Highly selective anodic monofluorination of 4-arylthio-1,3-dioxolan-2-ones: a marked solvent effect on product selectivity [J].
Ishii, H ;
Yamada, N ;
Fuchigami, T .
CHEMICAL COMMUNICATIONS, 2000, (17) :1617-1618
[4]   Solvation states and properties of binary mixtures of halogenated cyclic carbonates and a linear carbonate [J].
Katayama, H ;
Arai, J ;
Akahoshi, H .
JOURNAL OF POWER SOURCES, 1999, 81 :705-708
[5]  
KOBAYASHI M, 1999, P INT C FLUOR CHEM Y, P74
[6]   ELECTROCHEMICAL FLUORINATION OF AROMATIC-COMPOUNDS IN LIQUID R4NF.MHF .1. BASIC PROPERTIES OF R4NF.MHF AND THE FLUORINATION OF BENZENE, FLUOROBENZENE AND 1,4-DIFLUOROBENZENE [J].
MOMOTA, K ;
MORITA, M ;
MATSUDA, Y .
ELECTROCHIMICA ACTA, 1993, 38 (08) :1123-1130
[7]   Direct fluorination of γ-butyrolactone [J].
Sasaki, Y ;
Ebara, R ;
Nanbu, N ;
Takehara, M ;
Ue, M .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 108 (01) :117-120
[8]   MOBILITY AND IONIC ASSOCIATION OF LITHIUM AND QUATERNARY AMMONIUM-SALTS IN PROPYLENE CARBONATE AND GAMMA-BUTYROLACTONE [J].
UE, M .
JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 1994, 141 (12) :3336-3342
[9]   CONDUCTIVITIES AND ION ASSOCIATION OF QUATERNARY AMMONIUM CARBOXYLATES IN GAMMA-BUTYROLACTONE [J].
UE, M ;
SATO, T ;
TAKEDA, M .
DENKI KAGAKU, 1993, 61 (09) :1080-1087
[10]   SELECTIVE ELECTROCHEMICAL FORMYL HYDROGEN-EXCHANGE FLUORINATION OF ALIPHATIC-ALDEHYDES TO PREPARE ACYL FLUORIDES USING HF-BASE SOLUTIONS [J].
YONEDA, N ;
CHEN, SQ ;
HATAKEYAMA, T ;
HARA, S ;
FUKUHARA, T .
CHEMISTRY LETTERS, 1994, (05) :849-850