Effects of Substituents on the Smiles Rearrangement of <I>O</I>-<I>s</I>-Triazmyl-2-aminophenoIs
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概要
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Several 4- or 5-substituted <I>O</I>-(<I>s</I>-triazinyl)-2-aminophenols were synthesized, and the kinetics of the Smiles rearrangement of these compounds have been studied spectrophotometrically in methanol, ethanol, and 2-propanol in order to make clear the effects of substituents on the rearrangement. Substituents in the <I>s</I>-triazine nucleus were found to affect the progress of the reaction to a great extent by changing the positive character of the triazine-ring carbon. On the other hand, a substituent in the aminophenol moiety affects both the nucleophilic reactivity of the attacking amino group and the stability of the leaving phenoxide anion or the reactivity of the <I>s</I>-triazinyl group, but the effect on the amino group was found to be predominant, the effect of a substituent in the aminophenol moiety was smaller than that of the substituents in the <I>s</I>-triazine nucleus.
- 公益社団法人 日本化学会の論文
著者
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Itagaki Takeshi
Department Of Cardiology Shizuoka Prefectual General Hospital
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Matsui Kohji
Department of Chemistry, Faculty of Engineering, Gunma University
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Itagaki Takeshi
Department of Chemistry, Faculty of Engineering, Gunma University
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Maeno Norio
Department of Chemistry, Faculty of Engineering, Gunma University
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Uno Seiichi
Department of Chemistry, Faculty of Engineering, Gunma University
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