The Photoreactions of Phenazines <I>via</I> a Semiquinone Radical. The Photoreductive Deacylation of 1- or 2-Acyloxyphenazine

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概要

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• The Photo-irradiation of a solution of 1- or 2-benzoyloxyphenazine in 2-propanol, followed by aeration, affords 1- or 2-hydroxyphenazine, benzaldehyde, isopropyl benzoate, and/or benzoic acid as the reaction products. The spectral change of the solution in the reaction process gives evidence of the fission of the acyl-to-oxygen bond. The addition of ferric chloride or dimethyl sulfate to the reaction system containing 1-benzoyloxyphena-zine in 2-propanol leads to the formation of isopropyl benzoate. When methanol instead of 2-propanol is used as the solvent, methyl benzoate is produced mainly. In cyclohexene as a hydrogen-donating solvent, benzaldehyde and an oxetane are obtained. The irradiation of a solution of 1-benzoyloxyphenazine in <I>t</I>-butyl alcohol or benzene gives no product, and the starting material is recovered in a 90–100% yield. 1-Benzoyloxyphenazhydrin, a photo-reduction intermediate, does not contribute to the formation of benzaldehyde. The intermediary formation of a semiquinoid form during irradiation brings about the fission of the acyl-to-oxygen bond, thus affording the corresponding aldehyde.

• 公益社団法人 日本化学会の論文

著者

• Inoue Hiroo

  Department Of Applied Chemistry College Of Engineering Osaka Prefecture University

• Imoto Eiji

  Department of Applied Chemistry College of Engineering The University of Osaka Prefecture

• Sugimoto Akira

  Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture

• Ochiai Tadao

  Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture

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