Formations and reactions of o-benzoquinone mono- and di-imines. I.

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概要

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• We have succeeded in obtaining <I>o</I>-benzoquinone monoimine (<I>o</I>-BQMI) and <I>o</I>-benzoquinone diimine (<I>o</I>-BQDI) by oxidizing <I>o</I>-aminophenol (<I>o</I>-AP) and <I>o</I>-phenylenediamine (<I>o</I>-PD), respectively, with freshly prepared lead dioxide at −10 °C in several organic solvents, and also with potassium hexacyanoferrate (III) in an aqueous buffer solution. The formations and reactions of <I>o</I>-BQMI and <I>o</I>-BQDI in aqueous buffer solution were investigated by a stopped flow technique together with a conventional electronic absorption measurements. Both <I>o</I>-BQMI and <I>o</I>-BQDI were formed in the pH range 8–12, and the hydrolysis of <I>o</I>-BQMI to produce <I>o</I>-benzoquinone was found in the pH range 6–8. Both <I>o</I>-BQMI and <I>o</I>-BQDI were found to be unstable at a room temperature to produce 2-aminophenoxazin-3-one (APZ) and 2,3-diaminophenazine (DAP), respectively, as the main products. The formation reactions of APZ and DAP were investigated by observing the spectroscopic course of the reactions in <I>o</I>-BQMI- <I>o</I>-AP and <I>o</I>-BQDI- <I>o</I>-PD system in diethyl ether.

• 公益社団法人 日本化学会の論文

著者

• Shirota Yasuhiko

  Department Of Applied Chemistry Faculty Of Engineering Osaka University

• Nogami Takashi

  Department Of Applied Physics And Chemistry The University Of Electro-communication

• Mikawa Hiroshi

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

• Yamada Masakazu

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

• Hishida Tadanori

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

• Nogami Takashi

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

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