Electrolytic partial fluorination of organic compounds. Part 41: Highly selective electrolytic fluorination of dimethoxyethane, its homologues, and crown ethers
H. Ishii et al., Electrolytic partial fluorination of organic compounds. Part 41: Highly selective electrolytic fluorination of dimethoxyethane, its homologues, and crown ethers, TETRAHEDRON, 56(45), 2000, pp. 8877-8881
The anodic fluorination of dimethyoxyethane (DME), and diethylene glycol di
methyl ether in acetonitrile containing a fluoride salt as a supporting ele
ctrolyte and a fluoride ion source using an undivided cell provided the cor
responding monofluoromethyl ethers as a main product in good yields. On the
other hand, anodic fluorination of crown ethers resulted in carbon-carbon
bond cleavage which led to the selective production of alpha,omega -difluor
o products with high yields. A carbon anode as well as a platinum anode was
found to be effective for the electrolytic fluorination when Et3N . 5HF wa
s used as the supporting electrolyte. (C) 2000 Elsevier Science Ltd. All ri
ghts reserved.