The <I>N</I><SUP>1</SUP>→<I>N</I><SUP>2</SUP> Migration of the <I>s</I>-Triazinyl Group of 4-Substituted <I>N</I><SUP>1</SUP>,<I>N</I><SUP>1</SUP>-Bis-(<I>s</I>-triazinyl)-<I>o</I>-phenylenediamines
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概要
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Several 4-substituted <I>N</I><SUP>1</SUP>-[bis-(diethylamino)-<I>s</I>-triazinyl]-<I>N</I><SUP>1</SUP>-(dimethoxy-<I>s</I>-triazinyl)-<I>o</I>-phenylenediamines were synthesized, and the migrations of the <I>s</I>-triazinyl group were investigated in these compounds. In methanol, every 4-substituted <I>N</I><SUP>1</SUP>,<I>N</I><SUP>1</SUP>-bis(<I>s</I>-triazinyl)-<I>o</I>-phenylenediamine gave only 4-substituted <I>N</I><SUP>1</SUP>-[bis-(diethylamino)-<I>s</I>-triazinyl]-<I>N</I><SUP>2</SUP>-(dimethoxy-<I>s</I>-triazinyl)-<I>o</I>-phenylenediamine by the migration of the dimethoxy-<I>s</I>-triazinyl group; the rearrangement was assumed to proceed through an intramolecular nucleophilic attack by the <I>ortho</I> amino group upon the ring carbon of the dimethoxy-<I>s</I>-triazinyl group. However, in the presence of a small amount of acid, the <I>N</I><SUP>1</SUP>→<I>N</I><SUP>2</SUP> migration of the bis(diethylamino)-<I>s</I>-triazinyl group occurred preferentially, and two kinds of rearranged products were obtained. The kinetics of the rearrangement have also been studied spectrophotometrically in methanol, and the effects of the substituents on the rearrangement have been discussed.
- 公益社団法人 日本化学会の論文
著者
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Nakamura Kenji
Department Of Anatomy Graduate School Of Medicine Osaka City University
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Matsui Kohji
Department of Chemistry, Faculty of Engineering, Gunma University
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Nohara Noboru
Department of Chemistry, Faculty of Engineering, Gunma University
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