Substituted Ethylene Dications

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  • 置換エチレンジカチオン
  • 置換エネレンジカチオン
  • チカン エネレンジ カチオン

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Abstract

Cryoscopy and nuclear magnetic resonance (NMR) spectroscopy showed that the species formed from β-nitrostyrenes in trifluoromethanesulfonic acid (TFSA) are O, O-diprotonated dications (N, N-dihydroxyiminium benzyl dications). Further studies demonstrated that nitroethylene in TFSA yielded the N, N-dihydroxyiminium methylium dication, which is stabilized probably by Y-delocalization, consisting of six delocalized electrons (two π-electrons of the olefinic bond and four electrons of lone pairs of two hydroxy groups) in the whole system. From an alternative point of view, these dipositive systems can be regarded as substituted ethylene dications. The intervention of related substituted ethylene dications is proposed in the reaction of diphenylmethyl cations bearing a ketone or an ester group which gives the fluorenes and phenylphenanthrol in TFSA. Direct observations of 1, 1-diaryl-2-hydroxy-2-methoxyethylene dications and 1, 1, 2-triaryl-2-hydroxyethylene dications by means of NMR spectroscopy supported the postulation.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 109 (1), 1-11, 1989

    The Pharmaceutical Society of Japan

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