Reaction of Aromatic N-Oxides with Dipolarophiles. X. : Role of Charge-Transfer Complexes in 1,3-Dipolar Cycloaddition of Pyridine N-Oxides to Phenyl Isocyanate

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概要

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• In the 1,3-dipolar cycloaddition reaction of 3-methylpyridine N-oxide with phenyl isocyanate, spectroscopic evidence indicates that phenyl isocyanate forms charge-transfer complexes with both pyridine N-oxide and aromatic solvents such as pyridine. In connection with the charge-transfer complex formation, the solvent effect on the site selectivity was investigated. The most prominent solvent effect was observed in the reaction using 3-methylpyridine as a solvent. The equilibrium constants for the interaction of 3-methylpyridine N-oxide with phenyl isocyanate in several solvents were found to be quite large, indicating that the reaction mixtures favor complex formation. The proton nuclear magnetic resonance (^1H-NMR) spectra of the mixtures show a high field shift of the methyl signal of 3-methylpyridine N-oxide due to charge-transfer complexation. Based on these results, the structure and role of the complexes are discussed.

• 公益社団法人日本薬学会の論文
• 1986-03-25

著者

• 松岡 俊和

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 原野 一誠

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 久野 拓造

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 原野 一誠

  熊本大学 薬

• 原野 一誠

  熊本大学薬学部

• 久野 拓三

  熊本大学薬学部

• 近藤 理円

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 村瀬 元治

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 村瀬 元治

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 近藤 理円

  Faculty Of Pharmaceutical Sciences Kumamoto University

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