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Imidazole-derived carbenes and their elusive tetraazafulvalene dimers

Jolly, Phillip I. and Zhou, Shengze and Thomson, Douglas W. and Garnier, Jean and Parkinson, John A. and Tuttle, Tell and Murphy, John A. (2012) Imidazole-derived carbenes and their elusive tetraazafulvalene dimers. Chemical Science, 3 (5). pp. 1675-1679. ISSN 2041-6520

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Abstract

Previous efforts to prepare tetraazafulvalenes derived from imidazolium salt precursors have met with little success (one anomalously favourable example is known), and this is in line with the predicted reactivity of these compounds. However, we now report the preparation of a series of these tetraazafulvalenes formed either by deprotonation of 1,3-dialkylimidazolium salts or by Birch reduction of biimidazolium salts. The tetraazafulvalenes are highly reactive; for example, they act as Super-Electron-Donors towards iodoarenes. The two most reactive examples are formed more efficiently by Birch reduction than by the deprotonation route. Nevertheless, even in cases where the deprotonation approach affords a low stationary concentration, the mixture of precursor salt and base still produces the same powerful reductive chemistry that is the hallmark of tetraazafulvalene electron donors.

Item type: Article
ID code: 37853
Keywords: N-heterocyclic carbenes , super-electron-donor, reagent, derivatives, stability, imidazol-2-yudenes, organocatalysis, diaminocarbenes, dimerization, catalysis, Chemistry, Chemistry(all)
Subjects: Science > Chemistry
Department: Faculty of Science > Pure and Applied Chemistry
Technology and Innovation Centre > Bionanotechnology
Related URLs:
    Depositing user: Pure Administrator
    Date Deposited: 24 Feb 2012 10:23
    Last modified: 28 Mar 2014 05:50
    URI: http://strathprints.strath.ac.uk/id/eprint/37853

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