Multifunctional hydrolytic catalyses. V. The reaction of o-substituted benzohydroxamic acids and p-nitrophenyl acetate.
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概要
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Salicylohydroxamic acid(SHA), <I>N</I>-methylsalicylohydroxamic acid(MSHA), and <I>N</I>-methylphthalohydroxamic acid(MPHA) were prepared and their acylation reactions with <I>p</I>-nitrophenyl acetate were studied in aqueous ethanol at 30 °C. Both the acidity and nucleophilicity of the hydroxamic acid group were affected by the functional <I>ortho</I>-substituents(–OH, –COOH). In particular, the undissociated hydroxamic acid group in the MPHA monoanion possessed nucleophilic reactivity. This was brought forth by the general base assistance of the adjacent carboxylate group, as confirmed by the presence of the solvent isotope effect of <I>k</I><SUP>H</SUP>⁄<I>k</I><SUP>D</SUP>=2.5. Only the hydroxamate anion acted as the nucleophile in all other cases.
- 公益社団法人 日本化学会の論文
著者
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Kunitake Toyoki
Department Of Chemical Engineering & Technology Faculty Of Engineering Kyushu University
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Ando Reiko
Department of Organic Syntheis, Faculty of Engineering, Kyushu University
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Okahata Yoshio
Department of Applied Chemistry, Kyushu University 36
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Hirotsu Sumio
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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