Carbo-Quinoids: Stability and Reversible Redox-Proaromatic Character towards Carbo-Benzenes

The carbo‐mer of the para‐quinodimethane core is stable within in a bis(9‐fluorenylidene) derivative. Oxidation of this carbo‐quinoid with MnO2 in the presence of SnCl2 and ethanol affords the corresponding p‐bis(9‐ethoxy‐fluoren‐9‐yl)‐carbo‐benzene. The latter can be in turn converted back into the...

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Bibliographic Details
Published in:Angewandte Chemie 2015-02, Vol.127 (9), p.2741-2744
Main Authors: Cocq, Kévin, Maraval, Valérie, Saffon-Merceron, Nathalie, Saquet, Alix, Poidevin, Corentin, Lepetit, Christine, Chauvin, Remi
Format: Article
Language:English
Subjects:
Alkine
Aromatizität
Chemistry
Chinodimethane
Derivatives
Ethanol
Ethyl alcohol
Heterocyclen
Hydrocarbons
Hydroquinone
Joining
Oxidation
Reduction
Röntgenbeugung
Stability
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Summary:The carbo‐mer of the para‐quinodimethane core is stable within in a bis(9‐fluorenylidene) derivative. Oxidation of this carbo‐quinoid with MnO2 in the presence of SnCl2 and ethanol affords the corresponding p‐bis(9‐ethoxy‐fluoren‐9‐yl)‐carbo‐benzene. The latter can be in turn converted back into the carbo‐quinoid by reduction with SnCl2, thus evidencing a chemical reversibility of the interconversion between a pro‐aromatic carbo‐quinoid and an aromatic carbo‐benzene, and is reminiscent of the behavior of the benzoquinone/hydroquinone redox couple (in the red–ox opposite sense). Vor und zurück: Das Carbomer des para‐Chinodimethanmotivs ist als Bestandteil eines Bis(9‐fluorenyliden)‐Derivats stabil. Die Oxidation des proaromatischen Carbochinoids mit MnO2 in Gegenwart von SnCl2 und Ethanol liefert aromatisches p‐Bis(9‐ethoxyfluoren‐9‐yl)carbobenzol, das durch Reduktion mit SnCl2 wieder in das Carbochinoid verwandelt werden kann.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201407889