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Synthesis and Properties of Vinylogous 6-(Cyclopentadienyl)pentafulvenes

Eiermann, Matthias ; Stowasser, Bernd ; Hafner, Klaus ; Bierwirth, Klaus ; Frank, Anette ; Lerch, Alexander ; Reußwig, Jürgen (2022):
Synthesis and Properties of Vinylogous 6-(Cyclopentadienyl)pentafulvenes. (Publisher's Version)
In: Chemische Berichte, 123 (6), pp. 1421-1431. Wiley, e-ISSN 1099-0682,
DOI: 10.26083/tuprints-00022379,

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Item Type: Article
Origin: Secondary publication service
Status: Publisher's Version
Title: Synthesis and Properties of Vinylogous 6-(Cyclopentadienyl)pentafulvenes
Language: English

The application of the principle of kinetic stabilization on vinylogous 6-(cyclopentadienyl)pentafulvenes 1 led to the synthesis of the di- and tetra-tert-butyl derivatives 7a – e and 8a - c. Their reactions with bases and acids form charged, heteroatom-free cyanine-type carbanionic 9a - e, 10a – e and carbocationic 11a – e, 12a – c species which were characterized with NMR and UV/Vis spectroscopy. Conclusions on the ion pair structures of the alkali metal salts 9a - e and 10a – c are drawn from the spectroscopic data. Additionally, in one case the behavior of the alkali metal salt 10b towards oxidants was studied by cyclic voltammetry and the structure of the corresponding hydrocarbon 8b was proved by X-ray structural analysis.

Journal or Publication Title: Chemische Berichte
Volume of the journal: 123
Issue Number: 6
Place of Publication: Darmstadt
Publisher: Wiley
Uncontrolled Keywords: Pentafulvene, derivatives / Alkali metal - carbanion pair structure / Cyclic voltammetry / Electrochemistry / Reversible pentafulvene protonation
Classification DDC: 500 Naturwissenschaften und Mathematik > 540 Chemie
Divisions: 07 Department of Chemistry > Organ Chemistry
Date Deposited: 22 Nov 2022 10:36
Last Modified: 21 Apr 2023 11:54
DOI: 10.26083/tuprints-00022379
Corresponding Links:
URN: urn:nbn:de:tuda-tuprints-223798
URI: https://tuprints.ulb.tu-darmstadt.de/id/eprint/22379
PPN: 507152638
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