N,N'-Difluoro-1,4-diazoniabicyclo[2.2.2]octane Salts, Highly Reactive and Easy-to-Handle Electrophilic Fluorinating Agents^<1)>

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A series of <i>N</i>,<i>N</i>′-difluoro-1,4-diazoniabicyclo[2.2.2]octane salts were synthesized in a pure form by the fluorination of 1,4-diazabicyclo[2.2.2]octane with F<sub>2</sub> diluted with N<sub>2</sub> in the presence of a Brønsted acid in fluoro alcohol or acetonitrile or by fluorination followed by a treatment with a different Brønsted or Lewis acid. Their complete structural assignment was made based on spectral and elemental analyses of the isolated crystals. A great through-bond interaction between the two N–F’s of the salt was observed on <sup>19</sup>F NMR. An assessment was made of the usefulness of <i>N</i>,<i>N</i>′-difluoro-1,4-diazoniabicyclo[2.2.2]octane bis(triflate), bis(HSO<sub>4</sub>), bis(BF<sub>4</sub>), and bis(SbF<sub>6</sub>) salts for electrophilic fluorination; the bis(BF<sub>4</sub>) salt was demonstrated to be widely applicable as a highly reactive and easy-to-handle fluorinating agent. Thus, the bis(BF<sub>4</sub>) salt readily fluorinated activated aromatics, active methylene compounds or their salts, substituted styrenes, and vinyl acetates under mild conditions. It was shown that one N–F of the salt was effective for fluorination and that the other N–F played a role to activate fluorination through the bonds. Thus, the reaction mechanism was discussed, and fluorination followed by an immediate intramolecular one-electron transfer was suggested.

収録刊行物

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 69(8), 2287-2295, 1996-08-15

    公益社団法人 日本化学会

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