Solvolysis of Organic Phosphates. VIII. γ-Elimination in the Spontaneous Hydrolysis of 2-Chloro-3-pyridylmethyl Phosphate
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概要
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2-Chloro-3-pyridylmethyl phosphate was hydrolyzed in aqueous media. All runs were carried out in a pH range 1–3 where the reactive species are essentially of neutral and monoanion forms. The main reaction product was 3-hydroxymethyl-2-pyridone, the reaction following an apparent first-order kinetics with respect to both pyridone formation and liberation of inorganic phosphate. The hydrolytic elimination of the 2-chlorine atom was catalyzed to a great extent by the phosphate group. The dephosphorylation was effected by the presence of the 2-chlorine atom as well. The hydrolysis of the neutral phosphate species, which is in general inert to hydrolysis, was much accelerated in the present hydrolysis. A plausible mechanism was presented in terms of the concerted elimination of both 2-chlorine atom and phosphate moiety by their mutual catalytic participation. Besides the main reaction process, a normal hydrolysis affording 2-chloro-3-pyridylmethanol was also detected to proceed to a minor extent.
- 公益社団法人 日本化学会の論文
著者
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Murakami Yukito
Department Of Chemical Science And Technology Faculty Of Engineering Kyushu University
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SUNAMOTO JUNZO
Department of Applied Chemistry and Biotechnology, Niihama National College of Technology
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Sunamoto Junzo
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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Kanamoto Naomi
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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