The Beckmann Rearrangement of the Geometrical Isomers of Cyclohexyl Phenyl Ketoxime in Liquid Sulfur Dioxide

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概要

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• The Beckmann rearrangement of the isomeric cylcohexyl phenyl ketoximes was carried out in liquid sulfur dioxide at low temperature (–70°C) with thionyl chloride, benzenesulfonyl chloride, bromine and hydrogen halides. In liquid sulfur dioxide, the β-oxime was unstable and isomerized slowly to the α-oxime with no reagent. The α-oxime yielded <I>N</I>-cyclohexyl benzamide and the β-oxime yielded cyclohexanecarboxyanilide, respectively, by the Beckmann rearrangement in liquid sulfur dioxide. The geometrical structure of the isomers and isomerization between them were discussed. As for the β-oxime, the rate of the rearrangement by far surpassed the rate of the isomerization. The principle of the trans migration in the Beckmann rearrangement has been confirmed within the range of this experiment. The deoximation of the oxime to the parent ketone, cyclohexyl phenyl ketone was observed in the reaction of β-oxime with hydrogen chloride and bromide.

• 社団法人 日本化学会の論文

著者

• Tokura Niichiro

  Chemical Research Institute of Non-aqueous Solutions Tohoku University

• Tada Ritsuro

  Chemical Research Institute of Non-aqueous Solutions Tohoku University

• Masubuchi Yoichi

  Chemical Research Institute of Non-Aqueous Solutions Tohoku University

• Tada R.

  Chemical Research Institute of Non-Aqueous Solutions Tohoku University

関連論文

• Halogen Substitution in Liquid Sulfur Dioxide. I. Formation of Alkyl Halides from Alcohols and Halogens
• The Beckmann Rearrangement of the Geometrical Isomers of Cyclohexyl Phenyl Ketoxime in Liquid Sulfur Dioxide
• Retardation Effect Induced by Pyridine in the Radical Copolymerization of Styrene and Liquid Sulfur Dioxide

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