The Role of Oxygen in the Electrochemical Reduction of Ethyl 2-(2-(Bromomethyl)phenoxy)acetate at Carbon Cathodes in Dimethylformamide

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dc.contributor.authorSimon, Tamir
dc.contributor.authorVasquez, Antonio
dc.contributor.authorKelcher, Austin R.
dc.contributor.authorOlivares, Jacob A.
dc.contributor.authorJi, Chang
dc.date.accessioned2021-08-24T18:00:32Z
dc.date.available2021-08-24T18:00:32Z
dc.date.issued2020-02
dc.description.abstractCyclic 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.
dc.description.departmentChemistry and Biochemistry
dc.formatText
dc.format.extent5 pages
dc.format.medium1 file (.pdf)
dc.identifier.citationSimon, 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).
dc.identifier.doihttps://doi.org/10.1149/1945-7111/ab72ef
dc.identifier.issn1945-7111
dc.identifier.urihttps://hdl.handle.net/10877/14440
dc.language.isoen
dc.publisherIOP Science
dc.rights.holder© 2020 The Author(s).
dc.rights.licenseThis work is licensed under a Creative Commons Attribution 4.0 International License.
dc.sourceJournal of The Electrochemical Society, 2020, Vol. 167, No. 4, Article 045502.
dc.subjectcarbon cathodes
dc.subjectdimethylformamide
dc.subjectelectrochemical reduction
dc.subjectChemistry and Biochemistry
dc.titleThe Role of Oxygen in the Electrochemical Reduction of Ethyl 2-(2-(Bromomethyl)phenoxy)acetate at Carbon Cathodes in Dimethylformamide
dc.typeArticle

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