Formation and molecular structure of the 2:1-adducts of 1-alkoxy-2-benzopyrylium-4-olates with carbon disulfide.
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概要
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The Rh<SUB>2</SUB>(OAc)<SUB>4</SUB>-catalyzed decomposition of alkyl <I>o</I>-(diazoacetyl)benzoates in the presence of carbon disulfide gave two 2 : 1-adducts of the intermediate 1-alkoxy-2-benzopyrylium-4-olates with carbon disulfide together with a small amount of 5-(<I>o</I>-alkoxycarbonylphenyl)-1,3-oxathiole-2-thiones. The intramolecular carbene-carbonyl reaction of the carbenoid generated by the decomposition of the diazo ketones was clarified to be much faster than the intermolecular attack on carbon disulfide. The molecular structure of the major 2 : 1-adduct of 1-methoxy-2-benzopyrylium-4-olate with carbon disulfide was determined by means of X-ray crystallography. The crystals of the adduct are triclinic with space group <I>P</I>\bar1, and with the unit-cell dimensions of <I>a</I>=12.213(1), <I>b</I>=11.846(1), <I>c</I>=7.0403(2) Å, α=93.395(6), β=102.147(5), γ=109.536(7)°, and <I>Z</I>=2. The final <I>R</I> value is 0.044 for 2597 observed reflections. The structure was confirmed to be (S-<I>endo</I>, S′-<I>endo</I>).
- 公益社団法人 日本化学会の論文
著者
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Ibata Toshikazu
Institute Of Chemistry College Of General Education Osaka University
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TAMURA Hatsue
Institute of Chemistry, College of General Education, Osaka University
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Nakano Hirofumi
Institute of Chemistry, College of General Education, Osaka University
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