金属ストロンチウムを用いる新しい合成手法の開発  [in Japanese] The Development of the New Synthetic Methods Using Metallic Strontium  [in Japanese]

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Author(s)

    • 三好 徳和 MIYOSHI Norikazu
    • 徳島大学総合科学部総合数理学科 Department of Chemistry, Faculty of Integrated Arts and Sciences, The University of Tokushima
    • 松尾 強 MATSUO Tsuyoshi
    • 徳島大学総合科学部総合数理学科 Department of Chemistry, Faculty of Integrated Arts and Sciences, The University of Tokushima
    • 菊池 淳 [他] KIKUCHI Makoto
    • 徳島大学総合科学部総合数理学科 Department of Chemistry, Faculty of Integrated Arts and Sciences, The University of Tokushima
    • 和田 眞 WADA Makoto
    • 徳島大学総合科学部総合数理学科 Department of Chemistry, Faculty of Integrated Arts and Sciences, The University of Tokushima

Abstract

We found the interesting results that alkylation of carboxylic acids with methyl iodide using strontium metal proceeded smoothly to afford the corresponding monomethylated ketones, rather than the dimethylated alcohols, preferentially in moderate to good yields. Using the carboxylic acid sodium salt, the yield decreases slightly, but the reaction controls the over–addition of methyla-ting agent to give the dramatically improvement with high selectivities. Next, when benzoic acid reacted with metallic strontium and alkyl iodides, the unexpected reactions occurred to give <I>p</I>–alkylated products of the aromatic ring of benzoic acid in a trace amount. We were interested in the <I>p</I>–allylated product because this allylation reaction is unusual in these conditions and there are only a few reports of the <I>p</I>–alkylation of aromatic carbonyl compounds. As the results of various investigations, the <I>p</I>–alkylated products were obtained predominantly in good yields. Furthermore, it was found that the convenient bulky <I>tert</I>–benzylic alcohol benzoates were prepared by the dialkylation of methyl benzoate with methyl or <I>i</I>–butyl iodide in the presence of metallic strontium, followed by the addition of benzoyl chloride, benzoic anhydride or acetic anhydride as two portions.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 67(12), 1274-1281, 2009-12-01

    The Society of Synthetic Organic Chemistry, Japan

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Codes

  • NII Article ID (NAID)
    10026867321
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    ART
  • ISSN
    00379980
  • NDL Article ID
    10520401
  • NDL Source Classification
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL Call No.
    Z17-256
  • Data Source
    CJP  NDL  J-STAGE 
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