Leonard Y.M. Eymann
Synthesis of Organic Super-Electron-Donors by Reaction of Nitrous Oxide with N‐Heterocyclic Olefins
Eymann, Leonard Y.M.; Varava, Paul; Shved, Andrei M.; Curchod, Basile F.E.; Liu, Yizhu; Planes, Ophelie M.; Sienkiewicz, Andrzej; Scopelliti, Rosario; Fadaei Tirani, Farzaneh; Severin, Kay
Authors
Paul Varava
Andrei M. Shved
Dr Basile Curchod basile.f.curchod@durham.ac.uk
Academic Visitor
Yizhu Liu
Ophelie M. Planes
Andrzej Sienkiewicz
Rosario Scopelliti
Farzaneh Fadaei Tirani
Kay Severin
Abstract
The reaction of nitrous oxide (N2O) with N-heterocyclic olefins (NHOs) results in cleavage of the N–O bond and formation of azo-bridged NHO dimers. The latter represent very electron-rich compounds with a low ionization energy. Cyclic voltammetry studies show that the dimers can be classified as new organic super-electron-donors, with a reducing power similar to what is found for tetraazafulvalene derivatives. Mild oxidants are able to convert the neutral dimers into radical cations, which can be isolated. Further oxidation gives stable dications.
Citation
Eymann, L. Y., Varava, P., Shved, A. M., Curchod, B. F., Liu, Y., Planes, O. M., …Severin, K. (2019). Synthesis of Organic Super-Electron-Donors by Reaction of Nitrous Oxide with N‐Heterocyclic Olefins. Journal of the American Chemical Society, 141(3), 17112-17116. https://doi.org/10.1021/jacs.9b10660
Journal Article Type | Article |
---|---|
Acceptance Date | Oct 14, 2019 |
Online Publication Date | Oct 17, 2019 |
Publication Date | Oct 30, 2019 |
Deposit Date | Oct 16, 2019 |
Publicly Available Date | Mar 29, 2024 |
Journal | Journal of the American Chemical Society |
Print ISSN | 0002-7863 |
Electronic ISSN | 1520-5126 |
Publisher | American Chemical Society |
Peer Reviewed | Peer Reviewed |
Volume | 141 |
Issue | 3 |
Pages | 17112-17116 |
DOI | https://doi.org/10.1021/jacs.9b10660 |
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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.9b10660
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