化学
苯并恶唑
电化学
组合化学
键裂
阳离子聚合
直接的
电子转移
机制(生物学)
计算化学
光化学
有机化学
物理化学
电极
催化作用
哲学
物理
认识论
核物理学
单重态
激发态
作者
Tile Gieshoff,Anton Kehl,Dieter Schollmeyer,Kevin D. Moeller,Siegfried R. Waldvogel
摘要
The electrochemical synthesis of pyrazolidine-3,5-diones and benzoxazoles by N-N bond formation and C,O linkage, respectively, represents an easy access to medicinally relevant structures. Electrochemistry as a key technology ensures a safe and sustainable approach. We gained insights in the mechanism of these reactions by combining cyclovoltammetric and synthetic studies. The electron-transfer behavior of anilides and dianilides was studied and led to the following conclusion: The N-N bond formation involves a diradical as intermediate, whereas the benzoxazole formation is based on a cationic mechanism. Besides these studies, we developed a synthetic route to mixed dianilides as starting materials for the N-N coupling. The compatibility with valuable functionalities like triflates and mesylates for follow-up reactions as well as the comparison of different electrochemical set-ups also enhanced the applicability of this method.
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