Electrolytic partial fluorination of organic compounds 38.: Solvent effects on electrolytic fluorination of ethyl α-(2-pyrimidylthio) acetate

被引：10

作者：

Hou, Y ^{[1
]}

Fuchigami, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Elect Chem, Midori Ku, Yokohama, Kanagawa 2268502, Japan

来源：

ELECTROCHEMISTRY COMMUNICATIONS | 1999年 / 1卷 / 10期

关键词：

anodic partial fluorination; solvent effect; fluoro compound; 1,2-dimethoxyethane; sulfide;

D O I：

10.1016/S1388-2481(99)00094-6

中图分类号：

O646 [电化学、电解、磁化学];

学科分类号：

081704 ;

摘要：

Electrolytic partial fluorination of ethyl alpha-2-(pyrimidylthio) acetate was comparatively studied in acetonitrile and 1,2-dimethoxyethane (DME) containing Et4NF . 4HF as a supporting electrolyte and a fluoride ion source. Acetontrile was not suitable for the fluorination due to the severe anode passivation. In contrast, use of DME provided the corresponding ol-monofluorinated product in quantitative yield. A mixed electrolytic solvent of DME and acetonitrile was also effective for the fluorination and the product yield increased with an increase of the ratio of DME to acetonitrile. The superiority of DME can be explained mainly in terms of both the suppression of the anode passivation and enhancement of the nucleophilicity of fluoride ions. (C) 1999 Elsevier Science S.A. All rights reserved.

引用

页码：445 / 448

页数：4

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