Tetrahedron

Electrolytic partial fluorination of organic compound. Part: 53 Highly regioselective anodic mono-and difluorination of 4-arylthio-1, 3-dioxolan-2-ones. A marked solvent …

H Ishii, N Yamada, T Fuchigami

Index: Ishii, Hideki; Yamada, Norihisa; Fuchigami, Toshio Tetrahedron, 2001 , vol. 57, # 44 p. 9067 - 9072

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Citation Number: 24

Abstract

Anodic fluorination of 4-arylthio-1, 3-dioxolan-2-ones was investigated using various supporting fluoride salts and solvents. Their fluoro-desulfurization took place predominantly in Et4NF· 5HF/CH2Cl2 while the use of Et4NF· 4HF/DME resulted in α-fluorination, without the desulfurization, selectively. Electrolytic solvents affected markedly the product selectivity as compared with supporting fluoride salts. This is the first example of a solvent effect on ...