Title: Electrochemical Deconstructive Methoxylation of Arylalcohols – A Synthetic and Mechanistic Investigation: data
Citation
Maashi HA, Lewis-Atwell T, Harnedy J, et al. (2024). Electrochemical Deconstructive Methoxylation of Arylalcohols – A Synthetic and Mechanistic Investigation: data. Cardiff University. https://doi.org/10.17035/d.2024.0325653068
Access Rights: Creative Commons Attribution 4.0 International
Access Method: https://doi.org/10.17035/d.2024.0325653068 will take you to the repository page for this dataset, where you will be able to download the data or find further access information, as appropriate.
Dataset Details
Publisher: Cardiff University
Date (year) of data becoming publicly available: 2024
Data format: .txt, .inmr, .info, .par, .xml, .pdf, .temp, .back, .jpg, .ispd
Software Required: An appropriate NMR processing software is required for raw NMR data files
Estimated total storage size of dataset: Less than 1 gigabyte
DOI : 10.17035/d.2024.0325653068
DOI URL: http://doi.org/10.17035/d.2024.0325653068
Related URL: http://blogs.cardiff.ac.uk/themorrillgroup/
Herein, we report a mechanistic investigation of a recently developed electrochemical method for the deconstructive methoxylation of arylalcohols. A combination of synthetic, electroanalytical, and computational experiments have been performed to gain a deeper understanding of the reaction mechanism and the structural requirements for fragmentation to occur. It was found that 2-arylalcohols undergo anodic oxidation to form the corresponding aromatic radical cations, which fragment to form oxocarbenium ions and benzylic radical intermediates via mesolytic cleavage, with further anodic oxidation and trapping of the benzylic carbocation with methanol to generate the observed methyl ether products. It was also found that the electrochemical fragmentation of 2-arylalkanols is promoted by structural features that stabilize the oxocarbenium ions and/or benzylic radical intermediates formed upon mesolytic cleavage of the aromatic radical cations. With an enhanced understanding of the reaction mechanism and the structural features that promote fragmentation, it is anticipated that alternative electrosynthetic transformations will be developed that utilize this powerful, yet underdeveloped, mode of substrate activation. Analysis of reaction products from this methodology resulted in the following data: 1H, 19F and 13C NMR raw data files IR spectra High-Resolution Mass Spectrography spectra.
Description
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