The ozonolysis of quinoline, 6,7‐dimethylquinoline, 5,8‐dimethylquinoline, and 2,3‐dimethylquinoline in connection with the reactivity of the bonds in the ring system
The ozonolysis of quinoline, 6,7‐dimethylquinoline, 5,8‐dimethylquinoline, and 2,3‐dimethylquinoline in connection with the reactivity of the bonds in the ring system
复制标题
喹啉、6,7-二甲基喹啉、5,8-二甲基喹啉和2,3-二甲基喹啉的臭氧分解与环系中键的反应性
DOI：
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发表时间：
2010
期刊：
影响因子：
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通讯作者：
H. Boer
中科院分区：
文献类型：
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作者：
J. Wibaut;H. Boer
当臭氧作用于喹啉和某些二甲基喹啉时，主要反应是通过5，6 - 7，8-二叠氮化合物攻击苯环;这是臭氧分解后得到的产物。5，10-、6，7-和8，9-键不受臭氧影响。
因此，喹啉环系对臭氧的反应性与萘环系对相同试剂的反应性非常相似。喹啉环系中的5，6-和7，8-键对臭氧的作用方式与萘环系中的α，β-键相同。
在2，3-二甲基喹啉的臭氧分解中，除了乙二醛之外，还形成了二甲基乙二醛;这表明在主反应的旁边发生了副反应，其中通过将一个臭氧分子添加到3，4-键上来攻击吡啶环。
When ozone acts on quinoline and on some dimethylquinolines, the main reaction consists in an attack on the benzene ring, via a 5,6-7,8-diozonide; this follows from the products obtained after ozonolysis. The 5,10-, 6,7-, and 8,9-bonds are not affected by ozone.
The reactivity of the ring system of quinoline towards ozone therefore greatly resembles the reactivity of the ring system of naphthalene towards the same reagent. The 5,6- and 7,8-bonds in the quinoline ring system behave in the same manner towards ozone as do the α,β-bonds in the ring system of naphthalene.
Upon the ozonolysis of 2,3-dimethylquinoline, besides glyoxal there is also formed dimethylglyoxal; this points to the fact that by the side of the main reaction a side reaction takes place, in which the pyridine ring is attacked through addition of a molecule of ozone to the 3,4-bond.