Grant, Jacob A, Lu, Zhou, Tucker, David E et al. (6 more authors) (2017) New Blatter-type radicals from a bench-stable carbene. Nature Communications. p. 15088. ISSN 2041-1723
Abstract
Stable benzotriazinyl radicals (Blatter's radicals) recently attracted considerable interest as building blocks for functional materials. The existing strategies to derivatize Blatter's radicals are limited, however, and synthetic routes are complex. Here, we report that an inexpensive, commercially available, analytical reagent Nitron undergoes a previously unrecognized transformation in wet acetonitrile in the presence of air to yield a new Blatter-type radical with an amide group replacing a phenyl at the C(3)-position. This one-pot reaction of Nitron provides access to a range of previously inaccessible triazinyl radicals with excellent benchtop stabilities. Mechanistic investigation suggests that the reaction starts with a hydrolytic cleavage of the triazole ring followed by oxidative cyclization. Several derivatives of Nitron were prepared and converted into Blatter-type radicals to test the synthetic value of the new reaction. These results significantly expand the scope of using functionalized benzotriazinyls as stable radical building blocks.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © The Author(s) 2017 |
Keywords: | Journal Article |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 25 May 2017 11:15 |
Last Modified: | 21 Dec 2024 00:12 |
Published Version: | https://doi.org/10.1038/ncomms15088 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1038/ncomms15088 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:116925 |