Characterization of a Longicyclic (2,2,2,2) Conjugated π System in 1,4-Difluorobenzene-Naphthalene Biplanemer

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Author(s)

    • OKAMOTO Hideki
    • Department of Chemistry, Faculty of Science, Okayama University
    • SATAKE Kyosuke
    • Department of Chemistry, Faculty of Science, Okayama University
    • KIMURA Masaru
    • Department of Chemistry, Faculty of Science, Okayama University

Abstract

The electronic absorption spectrum of a 1,4-difluorobenzene–naphthalene biplanemer <b>1</b> exhibited a characteristic absorption band around 290 nm. This was attributable to intramolecular charge transfer interaction between the longicyclic conjugated π system and the benzene chromophore. The oxidation potential of <b>1</b> was 1.70 V (vs. Ag/AgCl), which was lower than those of the related compounds in which one of the double bonds of <b>1</b> was hydrogenated. Thermally, the biplanemer <b>1</b> underwent facile Cope rearrangement, followed by dehydrofluorination, to give 1-(4-fluorophenyl)naphthalene and 2-(3-fluorophenyl)naphthalene.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(12), 3557-3562, 1995-12-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008896672
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • Data Source
    CJP  J-STAGE 
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