Electrolytic partial fluorination of organic compounds. Part 60: Highly regioselective anodic fluorination of aryl propargyl sulfides

被引:13
作者
Riyadh, SM [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
electrochemical fluorination; alpha-monofluorinated; alpha-monofluoroallenyl sulfides;
D O I
10.1016/S0040-4020(02)00559-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aryl propargyl sulfides were subjected to electrochemical fluorination in dimethoxyethane (DME) containing various fluoride supporting electrolytes using an undivided cell to provide the corresponding alpha-monofluorinated or alpha,alpha-difluorinated sulfides selectively as main products in good yields depending on the amount of electricity passed. The alpha,alpha-difluorinated sulfides were stable enough to be isolated while the alpha-monofluorinated ones were very unstable. The alpha-monofluorinated sulfides were readily converted into the corresponding stable alpha-monofluoroallenyl sulfides in good yields. Furthermore, synthetic utility of alpha-monofluoroallenyl sulfides was also investigated. (C) 2002 Elsevier Science Ltd. All fights reserved.
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页码:5877 / 5883
页数:7
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