Photochemistry of Heterocyclic Compounds. VI. The Photochemical Behavior of Phenazine in Hydroxylic Solvents

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概要

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• The photochemical behavior of phenazine in acidified hydroxylic solvents varied with the concentration of acids present in the solutions. Irradiation of phenazine in an aqueous phosphoric acid afforded a 1 : 1 mixture of phenazinium and 1-hydroxyphenazinium cation radicals which were converted to a mixture of phenazine and 1-hydroxyphenazine. Irradiation in moderately strongly acidified alcohols (0.1–1.0 M HCl in alcohols) or in acetic acid containing 0.1 M <I>p</I>-toluenesulfonic acid yielded a 1 : 1 mixture of phenazine and the corresponding 1-alkoxyphenazines or 1-acetoxyphenazine after work-up of the reaction mixture. On the other hand, irradiation in a very strongly acidified methanol (5.6–9.6 M HCl in methanol) gave only the phenazinium cation radical. Mechanistic studies revealed that in the moderately strongly acidified media the reaction proceeds through a solvent-addition to the excited singlet phenazinium monocation, and in the very strongly acidified methanol the reaction proceeds through an electron transfer from the solvent to the excited singlet phenazinium dication.

• 公益社団法人 日本化学会の論文

著者

• Otsuji Yoshio

  Department Of Applied Chemistry College Of Engineering University Of Osaka Prefecture

• Imoto Eiji

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

• Wake Shigeo

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

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