Liquid Phase Chlorination of Olefins with Cupric Chloride. II. Stereochemistry of the Reactions of 2-Butenes and Cyclohexene

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概要

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• Chlorination of <I>cis</I>-and <I>trans</I>-2-butenes with cupric chloride yields a mixture of <I>meso</I>- and <I>dl</I>-2,3-dichlorobutanes with <I>meso/dl</I> ratio of about 60/40, which is almost independent of the starting olefin configuration. For cyclohexene, <I>trans</I>-1,2-dichlorocyclohexane is accompanied with the <I>cis</I>-dichloride, the amount of which depends upon the solvent polarities. In all cases the starting olefins and the product dichlorides are sufficiently stable under the reaction conditions. The results indicate that open ionic intermediates are involved in the chlorination of simple olefins in liquid phase reaction.

• 公益社団法人 日本化学会の論文

著者

• Koyano Takashi

  Central Research Laboratory, Toa Nenryo Kogyo Co.

関連論文

• On the Mechanism of Bromination of Olefins with Cupric Bromide
• Liquid Phase Chlorination of Olefins with Cupric Chloride
• Liquid Phase Chlorination of Olefins with Cupric Chloride. II. Stereochemistry of the Reactions of 2-Butenes and Cyclohexene

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