The Reaction of Di-t-butyl Peroxide with Aromatic Compounds in the Presence of Aluminum Chloride

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Other Title
  • 塩化アルミニウムの存在下における過酸化ジ-t-ブチルと芳香族化合物の反応

Description

The reaction of di-t-butyl peroxide with aromatic compounds such. as xylenes, anisole, chlorobenzene and bromobenzene was carried out in the presence of aluminum chloride at O. v 150C. Phenols were obtained in 2, v83% yield, accompanied by t-butylbenzenes in 14N72fO 5. yield. When o-dichlorobenzene was used as a solvent in the reaction with xylenes, xylenols were obtained in high yield (85 v93%e). However, the yield of xylenels decreased markedly in the presence of ethyl ether, nitromethane, or tetramethylene sulfone.<BR>Competitive oxygenations were carried out, and the relative reactivities of aromatie compounds to benzene were found to be in the following order:<BR>m--Xylene(132.1) Anisole(97.8) P-Xylene(60.3) e--Xylene(56.2) Chlerebenzene(O.08)<BR>The isomer distribution of phenols and the relative reactivities were compared with those of the oxygenation by t-butyl hydroperoxide-aluminum chloride previously reported.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1973 (7), 1301-1305, 1973-07-10

    The Chemical Society of Japan

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