Hydrogen Peroxide Oxidation. IV. A New Rearrangement Reaction of Phenyl Alkyl Ketones by Selenium Dioxide Catalyst

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概要

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• 1) Selenium dioxide catalyzed oxidation of phenyl alkyl ketone with hydrogen peroxide in <I>tert</I>-butyl alcohol gave α-phenyl carboxylic acid which was produced by the rearrangement of the phenyl group to the α-carbon atom as shown by Eqs. 2, 4 and 6. Therefore, the reaction mode is quite different from the Willgerodt reaction. The fact described above suggests that similar treatment may be generally applicable to the other aryl alkyl ketones.<BR>2) The reactivity of phenyl alkyl ketone was lower than that of dialkyl ketone, and cleavage reaction was also observed. It is assumed that the cleavage products may be produced partly from the Baeyer-Villiger oxidation product because an active species in this reaction system is considered to be peroxy-selenious acid, a kind of peracid.

• 社団法人 日本化学会の論文

著者

• Tsutsumi Shigeru

  Department of Chemical Technology Faculty of Engineering Osaka University

• Sonoda Noboru

  Department of Chemical Technology Faculty of Engineering Osaka University

• Sonoda N.

  Department of Chemical Technology Faculty of Engineering Osaka University

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• Hydrogen Peroxide Oxidation. IV. A New Rearrangement Reaction of Phenyl Alkyl Ketones by Selenium Dioxide Catalyst
• Oxidation of Alicyclic Compounds with Pernitrous Acid
• The Rearrangement Reaction of Levulinic Acid in a Selenium Dioxide-catalyzed Hydrogen Peroxide Oxidation
• Redox Reaction of Tetrahydrofuran Hydroperoxide
• Studies of Photochemical Reaction. VI. The Synthesis of Methylethyl-α-tetrahydrofurylcarbinol and Ethyl-α-tetrahydrofurylcarbinol

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