Lanthanoid(III) trichloride-tin(II) chloride mediated cycloaddition reaction of .ALPHA.,.ALPHA.'-dibromo ketones with 1,3-dienes or enamines.
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概要
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The reaction of α,α′-dibromo ketones with 1,3-dienes in the presence of CeCl<SUB>3</SUB>–SnCl<SUB>2</SUB> in tetrahydrofuran is found to give the corresponding [3+4] cycloadduct in fair to good yields under mild conditions. Furan and cyclopentadiene serve as highly efficient receptors of the oxyallyl intermediate to give bicyclic cycloadducts. The reaction of 2,4-dibromo-3-pentanone with isoprene gives both [3+4] and [3+2] cycloadducts. [3+2] Cycloaddition proceeds similarly with enamines to afford 2-cyclopenten-1-ones after treatment with 3% ethanolic NaOH solution.
- 公益社団法人 日本化学会の論文
著者
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Fukuzawa Shin-ichi
Department Of Applied Chemistry Chuo University
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Fujinami Tatsuo
Department of Material Science and Chemical Engineering, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Hamamatsu 432-8561, Japan
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Fukushima Masakazu
Department of Materials Science, Faculty of Engineering, Shizuoka University
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Sakai Shizuyoshi
Department of Applied Chemistry, Faculty of Engineering, Shizuoka University
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Fukuzawa Shin-ichi
Department of Materials Science, Faculty of Engineering, Shizuoka University
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