Synthesis and properties of a kinetically stabilized 9-silaphenanthrene

Norihiro Tokitoh, Akihiro Shinohara, Takeshi Matsumoto, Takahiro Sasamori, Nobuhiro Takeda, Yukio Furukawa

    Research output: Contribution to journalArticle

    33 Citations (Scopus)

    Abstract

    Reaction of 9-bromo-9,10-dihydro-9-silaphenanthrene (6) with lithium diisopropylamide (LDA) in THF at room temperature afforded kinetically stabilized 9-silaphenanthrene la bearing an efficient steric protection group, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt). 9-Silaphenanthrene la was isolated as pale yellow crystals, and the structure of la was completely determined by spectroscopic and X-ray crystallographic analyses. The 1H and 13C NMR chemical shifts corresponding to the 9-silaphenanthrene ring of la were observed in a typical aromatic region, while the central silicon atom showed the characteristic signal at 86.9 ppm in the 29Si NMR in C6D6. The 9-silaphenanthrene ring of la showed completely planar geometry, indicating that 9-silaphenanthrene has a delocalized 14π-electron system as an aromatic compound. In spite of its high thermal stability, la still has high reactivity at the 9,10position toward small reagents such as H2O.

    Original languageEnglish
    Pages (from-to)4048-4053
    Number of pages6
    JournalOrganometallics
    Volume26
    Issue number16
    DOIs
    Publication statusPublished - 2007 Jul 30

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    Bearings (structural)
    Nuclear magnetic resonance
    nuclear magnetic resonance
    aromatic compounds
    Aromatic compounds
    rings
    Chemical shift
    Silicon
    synthesis
    reagents
    chemical equilibrium
    Thermodynamic stability
    thermal stability
    reactivity
    lithium
    X rays
    Atoms
    Crystals
    Geometry
    Electrons

    ASJC Scopus subject areas

    • Inorganic Chemistry
    • Organic Chemistry

    Cite this

    Tokitoh, N., Shinohara, A., Matsumoto, T., Sasamori, T., Takeda, N., & Furukawa, Y. (2007). Synthesis and properties of a kinetically stabilized 9-silaphenanthrene. Organometallics, 26(16), 4048-4053. https://doi.org/10.1021/om700347z

    Synthesis and properties of a kinetically stabilized 9-silaphenanthrene. / Tokitoh, Norihiro; Shinohara, Akihiro; Matsumoto, Takeshi; Sasamori, Takahiro; Takeda, Nobuhiro; Furukawa, Yukio.

    In: Organometallics, Vol. 26, No. 16, 30.07.2007, p. 4048-4053.

    Research output: Contribution to journalArticle

    Tokitoh, N, Shinohara, A, Matsumoto, T, Sasamori, T, Takeda, N & Furukawa, Y 2007, 'Synthesis and properties of a kinetically stabilized 9-silaphenanthrene', Organometallics, vol. 26, no. 16, pp. 4048-4053. https://doi.org/10.1021/om700347z
    Tokitoh N, Shinohara A, Matsumoto T, Sasamori T, Takeda N, Furukawa Y. Synthesis and properties of a kinetically stabilized 9-silaphenanthrene. Organometallics. 2007 Jul 30;26(16):4048-4053. https://doi.org/10.1021/om700347z
    Tokitoh, Norihiro ; Shinohara, Akihiro ; Matsumoto, Takeshi ; Sasamori, Takahiro ; Takeda, Nobuhiro ; Furukawa, Yukio. / Synthesis and properties of a kinetically stabilized 9-silaphenanthrene. In: Organometallics. 2007 ; Vol. 26, No. 16. pp. 4048-4053.
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