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Synthesis of organic super-electron-donors by reaction of nitrous oxide with N‐Heterocyclic Olefins.

Eymann, Leonard Y. M. and Varava, Paul and Shved, Andrei M. and Curchod, Basile F. E. and Liu, Yizhu and Planes, Ophelie M. and Sienkiewicz, Andrzej and Scopelliti, Rosario and Fadaei Tirani, Farzaneh and Severin, Kay (2019) 'Synthesis of organic super-electron-donors by reaction of nitrous oxide with N‐Heterocyclic Olefins.', Journal of the American Chemical Society., 141 (3). pp. 17112-17116.


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.

Item Type:Article
Full text:(AM) Accepted Manuscript
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Publisher 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
Date accepted:14 October 2019
Date deposited:16 October 2019
Date of first online publication:17 October 2019
Date first made open access:17 October 2020

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