Formation of 1,3-oxathiole-2-thione and 1,2,4-trithiolane derivatives by the catalytic reaction of .ALPHA.-diazocarbonyl compounds with carbon disulfide.
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概要
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The rhodium(II) acetate-catalyzed decomposition of α-diazocarbonyl compounds such as substituted α-diazoacetophenones, cyclic diazoketones, cyclic diazodiketones, and α-diazo-β-ketoesters in carbon disulfide gave 1,3-oxathiole-2-thione derivatives in good yields. Diazomalonates also gave alkyl 5-alkoxy-2-thioxo-1,3-oxathiole-4-carboxylates together with 3,5-bis[bis(alkoxycarbonyl)methylene]-1,2,4-trithiolanes. The formation of 1,3-oxathiole-2-thiones can be explained by the intermediacy of zwitterionic intermediate containing rhodium(II) acetate formed by the reaction of carbon disulfide with ketocarbenoids generated in the catalytic decomposition of the diazocarbonyl compounds.
- 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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Nakano Hirofumi
Institute of Chemistry, College of General Education, Osaka University
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