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 effect on fluorinated product selectivity

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 Et(4)NF4HF/DME resulted in alpha -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 the fluorinated product selectivity in the anodic fluorination. (C) 2001 Elsevier Science Ltd. All rights reserved.