Electrolytic partial fluorination of organic compounds. Part 65: Regioselective anodic difluorination of oxazolyl sulfides

被引：9

作者：

Riyadh, SA ^{[1
]}

Ishii, H ^{[1
]}

Fuchigami, T ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2002年 / 58卷 / 45期

关键词：

electrochemical fluorination; 2-alkylthio-4,5-difluoro-4,5-dihydrooxazole; 2-alkylthio-2,5-difluoro-2,5-dihydrooxazole;

D O I：

10.1016/S0040-4020(02)01194-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrochemical fluorination of 2-alkylthio-4-methyloxazoles has been successfully carried out using Et4NF.nHF (n=4, 5) as the supporting electrolyte and fluoride source to provide the corresponding 2-alkylthio-4,5-difluoro-4-methyl-2-oxazolines, and fluorination did not take place at alpha to the sulfur atom. In the case of electrochemical fluorination of 2-methylthio-4-cabomethoxyoxazole afforded a 2,5-difluoro-3-oxazoline derivative in addition to a 4,5-difluoro-2-oxazoline one. In contrast, anodic fluorination of 2,4,5-trimethyloxazole devoid of a thio group resulted in no formation of fluorinated products. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：9273 / 9278

页数：6

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