Liquid Phase Chlorination of Olefins with Cupric Chloride
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Reactions of olefins with cupric chloride were studied in methanol at 100–140°C. The reactivity of olefins was in the order, ethylene>propylene>1-butene>2-butenes. A considerable amount of 1-chloro-2-methoxy compounds were found in the reaction products of 1-olefins. Competitive formation of dichloride and methoxychloride was suggested. Chlorination of 2-butenes leads to <I>meso</I>- and <I>dl</I>-2,3-dichlorobutanes, their ratio being invariable regardless of the starting material <I>cis</I>- or <I>trans</I>-2-butene. The mechanism is discussed in terms of ionic intermediates.
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関連論文
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- Liquid Phase Chlorination of Olefins with Cupric Chloride. II. Stereochemistry of the Reactions of 2-Butenes and Cyclohexene