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Reduction of π-expanded cyclooctatetraene with lithium: stabilization of the tetra-anion through internal Li+ coordination

The chemical reduction of a π-expanded polycyclic framework comprising a cyclooctatetraene moiety, octaphenyltetrabenzocyclooctatetraene, with lithium metal readily affords the corresponding tetra-anion instead of the expected aromatic dianion. As revealed by X-ray crystallography, the highly contor...

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Main Authors: Zhou, Zheng (Author) , Zhu, Yikun (Author) , Wei, Zheng (Author) , Bergner, John (Author) , Neiß, Christian (Author) , Doloczki, Susanne (Author) , Görling, Andreas (Author) , Kivala, Milan (Author) , Petrukhina, Marina A. (Author)
Format: Article (Journal)
Language:English
Published: 2021
In: Angewandte Chemie. International edition
Year: 2021, Volume: 60, Issue: 7, Pages: 3510-3514
ISSN:1521-3773
DOI:10.1002/anie.202013353
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/anie.202013353
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202013353
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Author Notes:Zheng Zhou, Yikun Zhu, Zheng Wei, John Bergner, Christian Neiß, Susanne Doloczki, Andreas Görling, Milan Kivala, and Marina A. Petrukhina
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Summary:The chemical reduction of a π-expanded polycyclic framework comprising a cyclooctatetraene moiety, octaphenyltetrabenzocyclooctatetraene, with lithium metal readily affords the corresponding tetra-anion instead of the expected aromatic dianion. As revealed by X-ray crystallography, the highly contorted tetra-anion is stabilized by coordination of two internally bound Li+, while two external cations remain solvent separated. The variable-temperature 7Li NMR spectra in THF confirm the presence of three types of Li+ ions and clearly differentiate internal binding, consistent with the crystal structure. Density-functional theory calculations suggest that the formation of the highly charged tetra-reduced carbanion is stabilized through Li+ coordination under the applied experimental conditions.
Item Description:First published: 27 October 2020
Im Titel ist das Pluszeichen bei "Li" hochgestellt
Gesehen am 18.09.2021
Physical Description:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.202013353

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