Molecular rearrangements. XXIX. Thermolysis of aromatic ketoximes.

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概要

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• Thermolysis of benzophenone <I>O</I>-benzoyloxime leads to the formation of NH<SUB>3</SUB>, CO<SUB>2</SUB>, benzene, biphenyl, benzophenone, benzanilide, benzonitrile, benzoic acid, 2-phenylbenzoxazole, salicylaldehyde and its <I>p</I>-isomer. Analogous results were also obtained on thermolysis of acetophenone <I>O</I>-benzoyloxime. Similarly, benzophenone and/or acetophenone <I>O</I>-benzyloximes give pyrolysis products of the same nature in addition to others corresponding to the benzyl moiety. Thermolysis of deoxybenzoin oxime gives NH<SUB>3</SUB>, toluene, benzonitrile, bibenzyl, benzil, benzyl alcohol, and 2-phenylindole. Moreover, its <I>O</I>-benzoyl ether affords in addition to these products, benzoic acid and benzyl benzoate. The main feature of these pyrolyses is the homolysis of the N–O bond together with either <I>O</I>-benzyl or <I>O</I>-benzoyl bonds providing free radicals that undergo different reactions involving H-abstraction, dimerization, fragmentation, rearrangement and cyclization to form the identified products.

• 公益社団法人 日本化学会の論文

著者

• Fahmy A.

  Chemistry Department, Faculty of Science, Assiut University

• Badr M.

  Chemistry Department, Faculty of Science, Assiut University

• Mahgoub S.

  Chemistry Department, Faculty of Science, Assiut University

• Aly M.

  Chemistry Department, Faculty of Science, Assiut University

• Atallah A.

  Chemistry Department, Faculty of Science, Assiut University

関連論文

• Molecular rearrangements. XXIX. Thermolysis of aromatic ketoximes.
• Condensation and cyclization reactions of 2-hydrazinobenzimidazole, -benzoxazole, and -benzothiazole.
• Molecular rearrangements. XXVIII. Thermolysis and photolysis of some hydroxamic acid derivatives.

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