The Syntheses and Reactions of Sulfenyl-substituted Sulfonium Ylides
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概要
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Unstable dimethylsulfonium (phenylthio)methylide (<B>2</B>) is prepared in a THF solution from the corresponding sulfonium salt by treating it with <I>n</I>-butyllithium. Sulfenyl-substituted stable phenacylides <B>6a</B> and <B>6b</B> are obtained in three ways. The ylide <B>6a</B> decomposes at 120°C in benzene to give (E)-<B>9</B>, the dimer of benzoyl(phenylthio)carbene. In contrast, the heating of <B>6a</B> in ethanol affords ethanolysis products (<B>11</B>, <B>12</B>) and ethyl benzoate. The alkylation of <B>6a</B> and <B>6b</B> with trimethyl- and triethyloxonium fluoroborate gives the vinylsulfonium salt <B>13</B>. The ylide <B>2</B> reacts with (Z)- and (E)-1,2-dibenzoylethylene and with diethyl fumarate to give cyclopropanes, <B>15</B> and <B>16</B> respectively.
- 公益社団法人 日本化学会の論文
著者
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Nozaki Hitosi
Department of Industrial Chemistry, Faculty of Engineering Kyoto University
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Hayasi Yosio
Department of Industrial Chemistry, Kyoto University
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