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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

Synthesis of Organic Super-Electron-Donors by Reaction of Nitrous Oxide with N‐Heterocyclic Olefins Thumbnail


Authors

Leonard Y.M. Eymann

Paul Varava

Andrei M. Shved

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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