Photochemistry of Heterocyclic Compounds. VII. The Photochemical Behavior of Phthalazine and Quinoxaline in Acidified Alcohols

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概要

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• Irradiation of phthalazine (<B>1</B>) and quinoxaline (<B>2</B>) in acidified methanol yielded 1-methylphthalazine (<B>3a</B>) and 2-methylquinoxaline (<B>4</B>), respectively. The quantum yields for the formation of 1-alkylphthalazines, which were obtained upon irradiation of <B>1</B> in acidified alcohols, varied with the sort of alcohols used and decreased in the order of methanol>ethanol>>2-propanol. When a mixture of <B>1</B> and 2,6-di-<I>t</I>-butylphenol (<B>6</B>) was irradiated in benzene containing trifluoroacetic acid under evacuated conditions, the oxidation of <B>6</B> occurred to form 3,5,3′,5′-tetra-<I>t</I>-butyldiphenoquinone (<B>7</B>) without destruction of <B>1</B>. Detailed mechanistic studies suggest that the photoalkylations of <B>1</B> and <B>2</B> in acidified alcohols proceed through an electron-transfer from solvents to an excited state of the protonated diazines.

• 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

• Takayama Yuichi

  Department Of Surgery Yachiyo Hospital

• 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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