Hyervalent Iodine Oxidation of Flavanones : A New Synthesis of Methyl 2-Aryl-2,3-kihydrobenzofuran-3-carboxylates by 1,2-Aryl Shift

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Abstract

Flavanones (<b>1</b>), on oxidation with (diacetoxyiodo)benzene-sulfuric acid (DIB–H<sub>2</sub>SO<sub>4</sub>) or (hydroxy)tosyloxy)iodo)benzene (HTIB) in trimethyl orthoformate, undergo facile ring contraction by 1,2-aryl shift, thereby yielding methyl 2-aryl-2,3-dihydrobenzofuran-3-carboxylates (<b>4</b>) as major products (40—80%). <i>cis</i>-3-Methoxyflavanones (<b>5</b>) and flavones (<b>3</b>) are the minor products formed in variable ratios.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(4), 1168-1171, 1995-04-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008888874
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • Data Source
    CJP  J-STAGE 
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