Effective Intramolecular Hydrogen Abstraction by the Sulfonamide Radical
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概要
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To study the reactivity of the sulfonamide radical in various reaction systems, the photodecomposition of <I>N</I>-<I>t</I>-butyl and <I>N</I>-methyl-<I>N</I>-chloroalkanesulfonamides was investigated. In benzene, the competitive hydrogen abstraction by the chlorine atom occurred to an appreciable extent and the participation of the chlorine atom was retarded with N<SUB>2</SUB>-flow control. In an aqueous solution (AcOH-H<SUB>2</SUB>O, <I>t</I>-BuOH-H<SUB>2</SUB>O), the quantitative conversion to γ-and δ-chloroalkanesulfonamide was observed; this was thought to be due to the intramolecular hydrogen abstraction by the sulfonamide radical and to the lowering of the reactivity of the chlorine atom because of the solvation by H<SUB>2</SUB>O. In an acid solution (AcOH-H<SUB>2</SUB>O-H<SUB>2</SUB>SO<SUB>4</SUB>), a higher preference for 1,5 hydrogen transfer was found; this was caused by the protonated sulfonamide radical. The formation ratio of γ- to δ-chloroalkanesulfonamide in several solvents was determined, and the reactivity of the sulfonamide radical was discussed. From the reaction products obtained, several aliphatic sultams were synthesized.
- 公益社団法人 日本化学会の論文
著者
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OKAHARA Mitsuo
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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Komori Saburo
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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Takeda Shinichi
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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Ohashi Takehisa
Department of Applied Chemistry, Faculty of Engineering, Osaka University
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