Formation and Reaction of Cyclohexanone Oxime Hydrogen Sulfate

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概要

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• Cyclohexanone oxime hydrogen sulfate, prepared by the reaction of cyclohexanone oxime with sulfur trioxide–1,4-dioxane complex under mild conditions, was isolated as stable salts with various Lewis bases. It was found that a Beckmann rearrangement of the oxime hydrogen sulfate to 3,4,5,6-tetrahydro-2<I>H</I>-azepin-7-ol hydrogen sulfate was retarded by the weak Lewis base 1,4-dioxane and prevented by a stronger Lewis base aniline. The rearrangement of the oxime hydrogen sulfate was also found to be promoted by Lewis acids such as sulfur trioxide, tin tetrachloride or zinc chloride. Hydrogen chloride retarded the rearrangement. Alcoholysis of the oxime hydrogen sulfate gave cyclohexanone oxime and monoalkyl sulfate quantitatively, while hydrolysis of the oxime hydrogen sulfate gave cyclohexanone, cyclohexanone oxime and ε-caprolactam.

• 公益社団法人 日本化学会の論文

著者

• Masaki Mitsuo

  Polymer Research Laboratory, Ube Industries, Ltd.

• Fukui Kiyoshi

  Polymer Research Laboratory, Ube Industries, Ltd.

• Uchida Masaru

  Polymer Research Laboratory, Ube Industries, Ltd.

関連論文

• Syntheses and spectral observation on the structure of several 2(1H)-pyridinethionato zinc complexes.
• Reaction of 3,4,5,6,-Tetrahydro-2H-azepin-7-ol Hydrogen Sulfate with Cyclohexanone Oxime–Tin Tetrachloride Complex
• The crystal and molecular structure of dichlorobis(2-pyridinethiolato)tin(IV).
• Formation and Reaction of Cyclohexanone Oxime Hydrogen Sulfate
• Deoxygenation of nitrobenzene by tributylphosphine in the presence of alcohols. Synthesis of 2-alkoxy-3H-azepines.
• Reaction of 3,4,5,6-Tetrahydro-2H-azepin-7-ol Hydrogen Sulfate with Nucleophilic Reagents
• Synthesis of dihalogenobis(2-pyridinethiolato)tin(IV) by the oxidative addition of disulfide to tin(II) halides-Consideration on the coordination structure.
• Syntheses of chlorozinc complexes of 2(1H)-pyridinethione and their mutual transformations.

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