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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| Hauptverfasser: | , , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
2021
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| In: |
Angewandte Chemie. International edition
Year: 2021, Jahrgang: 60, Heft: 7, Pages: 3510-3514 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.202013353 |
| Online-Zugang: | 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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| Verfasserangaben: | Zheng Zhou, Yikun Zhu, Zheng Wei, John Bergner, Christian Neiß, Susanne Doloczki, Andreas Görling, Milan Kivala, and Marina A. Petrukhina |
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| 245 | 1 | 0 | |a Reduction of π-expanded cyclooctatetraene with lithium |b stabilization of the tetra-anion through internal Li+ coordination |c Zheng Zhou, Yikun Zhu, Zheng Wei, John Bergner, Christian Neiß, Susanne Doloczki, Andreas Görling, Milan Kivala, and Marina A. Petrukhina |
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| 520 | |a 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. | ||
| 650 | 4 | |a density-functional calculations | |
| 650 | 4 | |a polycycles | |
| 650 | 4 | |a reduction | |
| 650 | 4 | |a structure elucidation | |
| 650 | 4 | |a X-ray diffraction | |
| 700 | 1 | |a Zhu, Yikun |e VerfasserIn |4 aut | |
| 700 | 1 | |a Wei, Zheng |e VerfasserIn |4 aut | |
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| 700 | 1 | |a Neiß, Christian |e VerfasserIn |4 aut | |
| 700 | 1 | |a Doloczki, Susanne |e VerfasserIn |4 aut | |
| 700 | 1 | |8 1\p |a Görling, Andreas |e VerfasserIn |0 (DE-588)1275955118 |0 (DE-627)1912207192 |4 aut | |
| 700 | 1 | |a Kivala, Milan |e VerfasserIn |0 (DE-588)120357231X |0 (DE-627)1688558489 |4 aut | |
| 700 | 1 | |a Petrukhina, Marina A. |e VerfasserIn |4 aut | |
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