Electrolytic partial fluorination of organic compounds. Part 41: Highly selective electrolytic fluorination of dimethoxyethane, its homologues, and crown ethers

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.