The Photochemical Reaction of Benzo[<I>c</I>]cinnoline. I. The Photoreduction and Subsequent Reactions in Acidified Alcohols

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概要

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• The photoinduced reaction of benzo[<I>c</I>]cinnoline (BCC) in strongly acidic aqueous alcohols, in which BCC exists in a monoprotonated form (BCCH<SUP>+</SUP>), was investigated. The initial step of the photoreaction was the hydrogen abstraction, which gave rise to 5,6-dihydroBCCH<SUP>+</SUP>, irrespective of the excitation wavelengths and the kind of alcohol (methanol, ethanol, or 2-propanol) used as a solvent. The subsequent reaction occurred upon irradiation by a light longer than 400 nm to afford 2,2′-diaminobiphenyl in ethanol, but not in methanol and 2-propanol. The 1-hydroxyethyl radical formed in the initial photoreduction appeared to participate in this reaction, donating its hydrogen atom to the ground-state 5,6-dihydroBCCH<SUP>+</SUP>. On the other hand, ultraviolet irradiation caused the subsequent photoreaction of 5,6-dihydroBCCH<SUP>+</SUP>, thus giving carbazole accompanied by the liberation of ammonia.

• 公益社団法人 日本化学会の論文

著者

• Inoue Hiroyasu

  Department Of Applied Chemistry Faculty Of Technology Kanagawa University

• TANAKA FUJIO

  Department of Chemistry, Faculty of Liberal Arts and Sciences, University of Osaka Prefecture

• Sakurai Tetsuo

  Department of Applied Chemistry, Faculty of Technology, Kanagawa University

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