Oxidizing Ability of a Series of (Tropon-2-ylimino)pnictoranes (Pnictogen=P, As, Sb, and Bi) toward Some Alcohols

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In order to gain a better understanding of the oxidizing ability of a series of (tropon-2-ylimino)pnictoranes of the general structure Ph<SUB>3</SUB>M=NR (R = tropon-2-yl; M = P, As, Sb, and Bi), reactions were run with some alcohols such as benzopinacol (1,1,2,2-tetraphenyl-1,2-ethanediol), benzoin, cinnamyl alcohol, 1-phenylethanol, a mixture of <I>cis</I>- and <I>trans</I>-4-<I>t</I>-butylcyclohexanol, 2-phenylethanol, and 1-phenyl-1,3-propandiol. Iminophosphorane oxidized only benzopinacol to give benzophenone, while both arsorane and stiborane oxidized benzopinacol and benzoin to give benzophenone and benzil, respectively. On the other hand, iminobismuthorane has appreciable oxidizing ability, and reacted with the alcohols mentioned above, except the primary alcohol, to give the corresponding carbonyl compounds. Iminobismuthorane reacted with 1-phenyl-1,3-propandiol selectively to oxidize benzyl alcohol moiety, but not a primary alcohol moiety, to give 3-hydroxy-1-phenyl-1-propanone. Thus, the oxidizing ability of a series of (tropon-2-ylimino)pnictoranes is demonstrated to be in the order of iminophosphorane < iminoarsorane < iminostiborane < iminobismuthorane: the dipolar (degree of contribution of the Ph<SUB>3</SUB>M<SUP>+</SUP>–<SUP>−</SUP>NR canonical structure) and electrophilic character of pnictogen elements of a series of iminopnictoranes appear to increase their oxidizing ability when the pnictogen stands lower in the periodic table.

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  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 76(5), 1029-1034, 2003-05-15

    The Chemical Society of Japan

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  • NII論文ID(NAID)
    10012812405
  • NII書誌ID(NCID)
    AA00580132
  • 本文言語コード
    ENG
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    ART
  • ISSN
    00092673
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    6532998
  • NDL 雑誌分類
    ZP1(科学技術--化学・化学工業)
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    Z53-B35
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