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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- PRAKASH Om
- Department of Chemistry, Kurukshetra University
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- TANWAR Madan P.
- Department of Chemistry, Kurukshetra University
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Author(s)
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- PRAKASH Om
- Department of Chemistry, Kurukshetra University
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- TANWAR Madan P.
- Department of Chemistry, Kurukshetra University
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
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 68(4), 1168-1171, 1995-04-15
The Chemical Society of Japan
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