Reaction of Benzoyl Peroxide with Phenols Substituted with Electron-Withdrawing Groups

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概要

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• Benzoyl peroxide has been allowed to react with various halogenophenols in boiling carbon tetrachloride and the nature of the products has been examined.<BR>2,4,6-Tribromophenol gave benzoic acid, polydibromophenylene oxide H(OC<SUB>6</SUB>H<SUB>2</SUB>Br<SUB>2</SUB>)<I><SUB>n</SUB></I>Br, 4-hydroxy-3,5,2′,4′,6′-pentabromodiphenyl ether, carbon dioxide and bromine, whereas in the case of 2,4,6-trichlorophenol the corresponding polymeric material could not be isolated, but <I>p</I>-benzoquinones substituted with chlorine and the 2,4,6-trichlorophenoxy group were formed. The reaction with 2,6-dichloro-and 2,6-dibromophenol gave a small amount of the corresponding 3,5,3′,5′-tetrahalogeno-4,4′-dihydroxybiphenyls, a type of product which were not obtained in the other cases. <I>p</I>-Halogenophenols yielded an appreciable amount of halogenocatechol monobenzoates.<BR><I>p</I>-Nitrophenol did not react with benzoyl peroxide in boiling carbon tetrachloride, but at 100°C in the absence of any solvent this phenol as well as the ortho isomer underwent reaction with evolution of considerable amount of carbon dioxide. These observations are discussed in terms of mechanisms involving free radicals.

• 社団法人 日本化学会の論文

著者

• TAKAMIZAWA Kanichiro

  Department of Applied Physics, Faculty of Engineering, Kyushu University

• INOUE H.

  Department of Basic and Behavioral Sciences, Division of Oral Biology, Northwestern University Denta

• Simamura Osamu

  Department of Chemistry Faculty of Science The University of Tokyo

• Takamizawa Kanichiro

  Department of Chemistry Faculty of Science The University of Tokyo

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