TEMPO-Me: An Electrochemically Activated Methylating Agent
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Norcott, Philip; Hammill, Chelsey; Noble, Dr Benjamin; Robertson, Johnathon C; Olding, Angus; Bissember, Alex C; Coote, Michelle
Description
Bench- and air-stable 1-methoxy-2,2,6,6-tetramethylpiperidine (TEMPO-Me) is relatively unreactive at ambient temperature in the absence of an electrochemical stimulus. In this report, we demonstrate that the one-electron electrochemical oxidation of TEMPO-Me produces a powerful electrophilic methylating agent in situ. Our computational and experimental studies are consistent with methylation proceeding via a SN2 mechanism, with a strength comparable to the trimethyloxonium cation. A protocol is...[Show more]
Collections | ANU Research Publications |
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Date published: | 2019-09-04 |
Type: | Journal article |
URI: | http://hdl.handle.net/1885/209107 |
Source: | Journal of the American Chemical Society |
DOI: | 10.1021/jacs.9b08634 |
Access Rights: | Open Access |
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TEMPO-Me- An Electrochemically Activated Methylating Agent.pdf | 938.81 kB | Adobe PDF |
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