The primary process of the photochemical isomerization of azanaphthalene N-oxides.

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概要

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• The quantum yields for the photochemical isomerization of azanaphthalene <I>N</I>-oxides, such as quinoline <I>N</I>-oxide and isoquinoline <I>N</I>-oxide, into lactam (Process I) or oxazepine (Process II) were determined in benzene (or carbon tetrachloride), in methanol, and in mixtures of the two solvents. Consequently, the reaction was revealed to be closely related to whether or not the <I>N</I>-oxide oxygen atom forms a hydrogen bond with the solvent molecule; that is, a strong hydrogen-bonding interaction between the excited singlet <I>N</I>-oxide and alcohol is essential for Process I, but not for Process II. It was further demonstrated that Process II occurred with the formation of powerful oxidants (probably oxaziridines) from the excited singlet <I>N</I>-oxide, whereas such an oxidizing species was not involved in Process I. The reaction mechanisms of Processes I and II were also discussed on the basis of the present experimental results.

• 公益社団法人 日本化学会の論文

著者

• Ono Isao

  Department Of Chemistry College Of Science And Engineering Aoyama Gakuin University

• Hata Norisuke

  Deparment of Chemistry, College of Science and Engineering, Aoyama Gakuin University

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