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...
Saved in:
| Main Authors: | , , , , , , , , |
|---|---|
| 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 
|
| Author Notes: | Zheng Zhou, Yikun Zhu, Zheng Wei, John Bergner, Christian Neiß, Susanne Doloczki, Andreas Görling, Milan Kivala, and Marina A. Petrukhina |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1770926968 | ||
| 003 | DE-627 | ||
| 005 | 20250323032823.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 210918s2021 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1002/anie.202013353 |2 doi | |
| 035 | |a (DE-627)1770926968 | ||
| 035 | |a (DE-599)KXP1770926968 | ||
| 035 | |a (OCoLC)1295678914 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 30 |2 sdnb | ||
| 100 | 1 | |a Zhou, Zheng |e VerfasserIn |0 (DE-588)1241416524 |0 (DE-627)1770926917 |4 aut | |
| 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 |
| 246 | 3 | 3 | |a Reduction of pi-expanded cyclooctatetraene with lithium$dstabilization of the tetra-anion through internal Li+ coordination |
| 264 | 1 | |c 2021 | |
| 300 | |a 5 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a First published: 27 October 2020 | ||
| 500 | |a Im Titel ist das Pluszeichen bei "Li" hochgestellt | ||
| 500 | |a Gesehen am 18.09.2021 | ||
| 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 | |
| 700 | 1 | |a Bergner, John |d 1995- |e VerfasserIn |0 (DE-588)1241416532 |0 (DE-627)1770926933 |4 aut | |
| 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 | |
| 773 | 0 | 8 | |i Enthalten in |t Angewandte Chemie. International edition |d Weinheim : Wiley-VCH, 1998 |g 60(2021), 7, Seite 3510-3514 |h Online-Ressource |w (DE-627)320497879 |w (DE-600)2011836-3 |w (DE-576)111552060 |x 1521-3773 |7 nnas |a Reduction of π-expanded cyclooctatetraene with lithium stabilization of the tetra-anion through internal Li+ coordination |
| 773 | 1 | 8 | |g volume:60 |g year:2021 |g number:7 |g pages:3510-3514 |g extent:5 |a Reduction of π-expanded cyclooctatetraene with lithium stabilization of the tetra-anion through internal Li+ coordination |
| 856 | 4 | 0 | |u https://doi.org/10.1002/anie.202013353 |x Verlag |x Resolving-System |z kostenfrei |3 Volltext |
| 856 | 4 | 0 | |u https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202013353 |x Verlag |z kostenfrei |3 Volltext |
| 883 | |8 1\p |a cgwrk |d 20250301 |q DE-101 |u https://d-nb.info/provenance/plan#cgwrk | ||
| 951 | |a AR | ||
| 992 | |a 20210918 | ||
| 993 | |a Article | ||
| 994 | |a 2021 | ||
| 998 | |g 120357231X |a Kivala, Milan |m 120357231X:Kivala, Milan |d 120000 |d 120100 |e 120000PK120357231X |e 120100PK120357231X |k 0/120000/ |k 1/120000/120100/ |p 8 | ||
| 998 | |g 1241416532 |a Bergner, John |m 1241416532:Bergner, John |d 120000 |d 120100 |e 120000PB1241416532 |e 120100PB1241416532 |k 0/120000/ |k 1/120000/120100/ |p 4 | ||
| 999 | |a KXP-PPN1770926968 |e 3979232433 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"type":{"media":"Online-Ressource","bibl":"article-journal"},"note":["First published: 27 October 2020","Im Titel ist das Pluszeichen bei \"Li\" hochgestellt","Gesehen am 18.09.2021"],"language":["eng"],"recId":"1770926968","titleAlt":[{"title":"Reduction of pi-expanded cyclooctatetraene with lithium$dstabilization of the tetra-anion through internal Li+ coordination"}],"person":[{"display":"Zhou, Zheng","roleDisplay":"VerfasserIn","role":"aut","family":"Zhou","given":"Zheng"},{"role":"aut","roleDisplay":"VerfasserIn","display":"Zhu, Yikun","given":"Yikun","family":"Zhu"},{"role":"aut","display":"Wei, Zheng","roleDisplay":"VerfasserIn","given":"Zheng","family":"Wei"},{"family":"Bergner","given":"John","display":"Bergner, John","roleDisplay":"VerfasserIn","role":"aut"},{"family":"Neiß","given":"Christian","roleDisplay":"VerfasserIn","display":"Neiß, Christian","role":"aut"},{"display":"Doloczki, Susanne","roleDisplay":"VerfasserIn","role":"aut","family":"Doloczki","given":"Susanne"},{"given":"Andreas","family":"Görling","role":"aut","display":"Görling, Andreas","roleDisplay":"VerfasserIn"},{"role":"aut","roleDisplay":"VerfasserIn","display":"Kivala, Milan","given":"Milan","family":"Kivala"},{"roleDisplay":"VerfasserIn","display":"Petrukhina, Marina A.","role":"aut","family":"Petrukhina","given":"Marina A."}],"title":[{"title_sort":"Reduction of π-expanded cyclooctatetraene with lithium","subtitle":"stabilization of the tetra-anion through internal Li+ coordination","title":"Reduction of π-expanded cyclooctatetraene with lithium"}],"physDesc":[{"extent":"5 S."}],"relHost":[{"recId":"320497879","corporate":[{"roleDisplay":"Herausgebendes Organ","display":"Gesellschaft Deutscher Chemiker","role":"isb"}],"language":["eng"],"type":{"bibl":"periodical","media":"Online-Ressource"},"disp":"Reduction of π-expanded cyclooctatetraene with lithium stabilization of the tetra-anion through internal Li+ coordinationAngewandte Chemie. International edition","note":["Gesehen am 20.12.2022","Fortsetzung der Druck-Ausgabe"],"titleAlt":[{"title":"Angewandte Chemie / International edition"}],"part":{"year":"2021","pages":"3510-3514","issue":"7","text":"60(2021), 7, Seite 3510-3514","volume":"60","extent":"5"},"pubHistory":["37.1998 -"],"title":[{"title":"Angewandte Chemie","subtitle":"a journal of the Gesellschaft Deutscher Chemiker","title_sort":"Angewandte Chemie","partname":"International edition"}],"physDesc":[{"extent":"Online-Ressource"}],"id":{"issn":["1521-3773"],"zdb":["2011836-3"],"doi":["10.1002/(ISSN)1521-3773"],"eki":["320497879"]},"origin":[{"publisherPlace":"Weinheim","dateIssuedDisp":"1998-","dateIssuedKey":"1998","publisher":"Wiley-VCH"}]}],"name":{"displayForm":["Zheng Zhou, Yikun Zhu, Zheng Wei, John Bergner, Christian Neiß, Susanne Doloczki, Andreas Görling, Milan Kivala, and Marina A. Petrukhina"]},"origin":[{"dateIssuedKey":"2021","dateIssuedDisp":"2021"}],"id":{"eki":["1770926968"],"doi":["10.1002/anie.202013353"]}} | ||
| SRT | |a ZHOUZHENGZREDUCTIONO2021 | ||