The Role of Oxygen in the Electrochemical Reduction of Ethyl 2-(2-(Bromomethyl)phenoxy)acetate at Carbon Cathodes in Dimethylformamide
Date
2020-02
Authors
Simon, Tamir
Vasquez, Antonio
Kelcher, Austin R.
Olivares, Jacob A.
Ji, Chang
Journal Title
Journal ISSN
Volume Title
Publisher
IOP Science
Abstract
Cyclic voltammetry (CV) and controlled-potential electrolysis (CPE) were employed to examine the direct reduction of ethyl 2-(2-(bromomethyl)phenoxy)acetate at carbon cathodes in dimethylformamide (DMF) containing tetramethylammonium tetrafluoroborate (TMABF<sub>4</sub>) as the electrolyte. Cyclic voltammogram of the substrate exhibits a single irreversible cathodic wave with a peak potential of –1.75 V vs SCE, which is characteristic for the reduction of organic halides in aprotic solvents. Bulk electrolyses of ethyl 2-(2-(bromomethyl)phenoxy)acetate were carried out in the absence and presence of oxygen. The product distributions were obtained by gas chromatograph (GC) as well as gas chromatograph coupled to a mass spectrometer (GC−MS). Two bicyclic compounds, ethyl 2,3-dihydro-1-benzofuran-2-carboxylate and ethyl benzofuran-2-carboxylate, were found to be formed in a total yield of more than 40% in the presence of oxygen. The reaction mechanism, in which the oxygen plays a significant role, was proposed and discussed on the basis of this study.
Description
Keywords
carbon cathodes, dimethylformamide, electrochemical reduction, Chemistry and Biochemistry
Citation
Simon, T., Vasquez, A., Kelcher, A. R., Olivares, J. A., & Ji, C. (2020). The role of oxygen in the electrochemical reduction of ethyl 2-(2-(Bromomethyl)phenoxy)acetate at carbon cathodes in dimethylformamide. Journal of the Electrochemical Society, 167(4).
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© 2020 The Author(s).
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This work is licensed under a Creative Commons Attribution 4.0 International License.