Halofluorination of Alkenes Using Dilute Hydrofluoric Acid

• Manabu Kuroboshi

  Research Laboratory of Resources Utilization, Tokyo Institute of Technology4259 Nagatsuta, Midori-ku, Yokohama, Kanagawa 226

• Tamejiro Hiyama

  Research Laboratory of Resources Utilization, Tokyo Institute of Technology4259 Nagatsuta, Midori-ku, Yokohama, Kanagawa 226

抄録

Iodofluorination of alkenes was achieved with N-iodosuccinimide, potassium hydrogendifluoride, and 1 M hydrofluoric acid using tetrabutylammonium fluoride as a phase-transfer catalyst. The active fluorinating reagent was shown to be tetrabutylammonium dihydrogentrifluoride by preparing the salt in a different way and by effecting the same transformation under anhydrous conditions. Bromofluorination of alkenes also was carried out using 1,3-dibromo-5,5-dimethylhydantoin. Treatment of the I–F adducts with DBU afforded fluoro olefins stereospecifically.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 68 (7), 1799-1805, 1995-07-01

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360002219104153344
• NII論文ID: 130004149234
• DOI: 10.1246/bcsj.68.1799
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/68/7/1799/56192672/bcsj.68.1799.pdf
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