Electrolytic partial fluorination of organic compounds. 36. Regioselectiveanodic fluorination of phenylthiolated benzofuranone and benzothiazole derivatives
S. Higashiya et al., Electrolytic partial fluorination of organic compounds. 36. Regioselectiveanodic fluorination of phenylthiolated benzofuranone and benzothiazole derivatives, J FLUORINE, 99(2), 1999, pp. 189-195
The anodic fluorination of 3-phenylthio-2-benzofuranones and alpha-phenylth
io-2-benzothiazolylacetonitrile was investigated. Both derivatives were sel
ectively fluorinated in good yields at the carbon alpha to the sulfur atoms
in Et4NF . 3HF/DME using a platinum anode and an undivided cell. The fluor
ination yields of the benzofuranone derivatives were improved by the additi
on of Ph2S, which was not effective in the case of the benzothiazole deriva
tive. The fluorination yield of the benzothiazole derivative was strongly a
ffected by the stirring state of the electrolytic solution or the applied a
node potential. (C) 1999 Elsevier Science S.A. All rights reserved.