Elemental fluorine. Part 24.[1]: Fluorination of ethers by fluorine and Selectfluor |
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Authors: | Richard D. Chambers Takashi Okazoe Emmanuelle Thomas |
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Affiliation: | a Department of Chemistry, University of Durham, South Road, Durham, DH1 3LE, UK b Asahi Glass Co., 1150, Hazawa-cho, Yokohama, Kanagawa, 221-8755, Japan |
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Abstract: | Reactions of dialkyl ethers with either fluorine or Selectfluor™ led to the formation of unusual difluorinated polyether products in modest yields. A mechanism involving initial fluorination of the site adjacent to ether oxygen followed by elimination of hydrogen fluoride, reaction of the generated enol system with a further equivalent of fluorinating agent giving an oxonium system which reacts with water during aqueous work-up to lead eventually to the products observed, is suggested. |
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Keywords: | Selective direct fluorination Electrophilic fluorination Fluorine Polyfluoroether Electrophilic aliphatic substitution |
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