Olefin Metathesis. III.

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  • ICHIKAWA Kazuaki
    Department of Applied Chemistry, Faculty of Engineering, Nagoya University
  • TAKAGI Toru
    Department of Applied Chemistry, Faculty of Engineering, Nagoya University
  • FUKUZUMI Kazuo
    Department of Applied Chemistry, Faculty of Engineering, Nagoya University

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Other Title
  • オレフィンメタセシス (第3報)
  • オレフィン メタセシス 3 キンイツケイ オレフィン メタセシス ニ オケル
  • Influence of the Reaction Medium on the Conversions in Homogeneous Olefin Metathesis
  • 均一系オレフィンメタセシスにおけるオレフィンの転化率に対する反応溶媒の影響

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In the homogeneous metathesis of 2-heptene catalyzed by WCl6-Et3Al and WCl6-R4Sn systems, the influence of the reaction medium on the conversion was investigated. Many kinds of halogenated hydrocarbon were found to be the more excellent medium than benzene and chlorobenzene. The polychlorinated aliphatic hydrocarbons, and polyhalogenated benzenes such as trichloroethylene, tetrachloroethylene, hexachloro-1, 3-butadiene, hexachlorocyclopentadiene, 1, 1, 2, 2-tetrachloroethane, o- and m-dichlorobenzene and 1, 2, 4-trichlorobenzene gave the good conversions without the formation of the undesirable Friedel-Crafts products. The optimum range of the ratio Et3Al/WCl6 and Olefin/WCl6 shifted depending upon the medium used. In the binary solvent systems of benzene-trichloroethylene, -1, 2, 4-trichlorobenzene and -m-dichlorobenzene, the best conversions were observed at 4045 volume% of the halogenated solvent. The metathesis was significantly inhibited by the addition of the compounds containing oxygen, sulfur, nitrogen and phosphorus atoms to the reaction medium. The mechanisms of the medium effects were discussed.

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