Structures and Tropicity of Hydrogenation Products of a Bisdehydro[13]annulenone and a Bisdehydro[15]annulenone

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Abstract

The catalytic partial hydrogenation of the 5,10-dimethyl-6,8-bisdehydro[13]annulenone using Pd–BaSO<sub>4</sub> afforded the 5,10-dimethyl[13]annulenone together with two isomeric 5,10-dimethyl-6-dehydro[13]annulenones. The dimethyl[13]annulenone, which is the first example of a monocyclic non-dehydro annulenone derivative larger than tropone, was found to be atropic on the basis of <sup>1</sup>H NMR spectra. Molecular mechanics studies indicate the extensive deviation of the molecular skeleton from planarity and help to explain the lack of peripheral conjugation. Attempts to obtain the [15]annulenone and the [17]annulenone from the bisdehydro[15]annulenone and the bisdehydro[17]annulenone, respectively, were unsuccessful.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 71(1), 221-230, 1998-01-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008927971
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4395768
  • NDL Source Classification
    ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-B35
  • Data Source
    CJP  NDL  J-STAGE 
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