Abstract
The influence of the acid components of the medium on the anodic 2,5-dimethoxy-phenylation of various azoles at the nitrogen atom was studied for constant-current electrolysis of the mixture azole—1,4-dimethoxybenzene in an undivided cell. Elimination of azole functions in the key steps of the process can be catalyzed by such electrophilic species as Brønsted (AcOH) and Lewis acids (ZnCl2) and even the radical cation generated in the anodic oxidation of 1,4-dimethoxybenzene. The data obtained provided evidence for the existence of the arenonium cation as a key reaction intermediate.
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V. A. Petrosyan, A. V. Burasov, Izv. Akad. Nauk, Ser. Khim., 2007, 2101 [Russ. Chem. Bull., Int. Ed., 2007, 56, 11].
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 285–290, February, 2008.
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Petrosyan, V.A., Burasov, A.V. The role of acid catalysis in the electrosynthesis of N-(2,5-dimethoxyphenyl)azoles. Russ Chem Bull 57, 292–297 (2008). https://doi.org/10.1007/s11172-008-0045-4
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DOI: https://doi.org/10.1007/s11172-008-0045-4