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Mechanism of Oxidative Alkoxyamine Cleavage: The Surprising Role of the Solvent and Supporting Electrolyte

Noble, Ben; Norcott, Philip; Hammill, Chelsey; Ciampi, Simone; Coote, Michelle

Description

In this work, we show that the nature of the supporting electrolyte and solvent can dramatically alter the outcome of the electrochemically mediated cleavage of alkoxyamines. A combination of cyclic voltammetry experiments and quantum chemistry is used to study the oxidation behavior of TEMPO-i-Pr under different conditions. In dichloromethane, using a noncoordinating electrolyte (TBAPF6), TEMPO-i-Pr undergoes reversible oxidation, which indicates that the intermediate radical cation is stable...[Show more]

CollectionsANU Research Publications
Date published: 2019-04-25
Type: Journal article
URI: http://hdl.handle.net/1885/203776
Source: Journal of Physical Chemistry C
DOI: 10.1021/acs.jpcc.9b01832
Access Rights: Open Access

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