Synthesis of Furan Derivatives. LXXXIV. Kinetic Studies of the Curtius Rearrangement of 5-Substituted 2-Furoyl Azides and Related Compounds
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概要
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Kinetic studies of the thermolytic Curtius rearrangement of set A of 5-substituted 2-furoyl azides (1-6), 5-substituted 2-thenoyl azides (7,8 and 9) and 2-pyrroyl azide (10), and set B of p-substituted benzoyl azides (11,12 and 13) and 2-, 3- and 4-pyridinemonocarbonyl azides (14,15 and 16) in toluene were executed by means of IR (infrared) spectrophotometric method. It was found through the relationship between log k and 1/T that the isokinetic temperature (Q) of the set A and B are Q=371°and 353°K, respectivery. Based on ΔE^=⃥ and ΔS^=⃥, it seems to be reasonable that the reactivity of the each of unsubstituted acyl azides (2,7,9 and 12) is very nearly parallel to that the each resonance energy of the parent rings of the above four acyl azides. Additionally, it was found that the substituent dependence on ΔS^=⃥ in the rearrangement of the 5-substituted 2-furoyl azides (2-6) and also the 5-substituted 2-thenoyl azides (9 and 10) is indifferent to whether the substituents are electron releasing or attracting groups, and on the other hand, the rearrangement of p-substituted benzoyl azides (12 and 13) has ΔS^=⃥ decreased, respectively.
- 公益社団法人日本薬学会の論文
- 1978-04-25
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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