Synthesis of Furan Derivatives. LXXXIII. Kinetics of Acyl Azide Formation of Carboxylic Acids with Diphenyl Phosphorazidate
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概要
- 論文の詳細を見る
5-Substituted 2-furoyl azides (7a, 7b and 7c), 5-substituted 2-thenoyl azides (7d, 7e and 7f), 2-, 3- and 4-pyridinemonocarbonyl azides (7j, 7k and 7l) and p-substituted benzoyl azides (7g, 7h and 7i) were prepared from the corresponding carboxylic acids with DPPA (4) in one step and in good yields, respectively. It was found through the kinetic studies that an electron-withdrowing group substituted at 5-position (furan and thiophene ring) or p-position (benzene ring) decreases the rate of the reaction, and reversely, an electron-donating substituted at 5- or p-position increases it. In addition, it looks to be reasonable that the most probable pathway is to form the above acyl azides via the activated six-membered cyclic complex (9) as an intermediacy and then to proceed in the concerted reaction, based on the activation energies (ΔE^*) and entropies (ΔS^*) obtained.
- 公益社団法人日本薬学会の論文
- 1977-07-25
著者
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北川 徳治郎
Faculty of Pharmaceutical Sciences
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北川 徳治郎
Faculty Of Pharmaceutical Sciences Kobe Gakuin University
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西海枝 東雄
Faculty of Pharmaceutical Sciences, Kobe Gakuin University
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西海枝 東雄
Faculty Of Pharmaceutical Sciences Kobe Gakuin University
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