A Kinetic Study of the Friedel-Crafts Phenylsulfonylation of Substituted Benzenes in Nitrobenzene

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  • 置換ベンゼン類のFriedel-Craftsフェニルスルホニル化反応の速度論的研究

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Friedel-Crafts reactions of substituted benzenes with benzenesulfonyl chloride for aluminum chloride in nitrobenzene have been studied kinetically. The rate data obtained in the case of vario us substituted benzenes, suggested the following reaction scheme. The rate constants k3(=k1.k2/k_1) were in good agreement with Hammett-type linear free energy relationships, Brown-Okamoto's σ+ (ρ=-5.3). It was found from the temperature effect on the isomer distribution that in phenylsulfonylation, (m-/p-) ratio of toluene and (o-/p-) ratio of anisole increased with temperature, but (o-/p-) ratio of toluene decreased. Differences in activation energies and activation entropies at the o- and p- positions and the m- and p-positions for toluene and the o- and p-positions for anisole were -0.27 kcal/mol, -O.71 e.u./mol, 0.92, 1.4, and 0.58, 0.33, respectively.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1987 (9), 1699-1704, 1987-09-10

    The Chemical Society of Japan

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