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Issue 5, 2012
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Imidazole-derived carbenes and their elusive tetraazafulvalene dimers

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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.

Graphical abstract: Imidazole-derived carbenes and their elusive tetraazafulvalene dimers

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Publication details

The article was received on 12 Jan 2012, accepted on 11 Feb 2012 and first published on 14 Feb 2012

Article type: Edge Article
DOI: 10.1039/C2SC20054F
Citation: Chem. Sci., 2012,3, 1675-1679

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    Imidazole-derived carbenes and their elusive tetraazafulvalene dimers

    P. I. Jolly, S. Zhou, D. W. Thomson, J. Garnier, J. A. Parkinson, T. Tuttle and J. A. Murphy, Chem. Sci., 2012, 3, 1675
    DOI: 10.1039/C2SC20054F

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