Carbo ‐Quinoids: Stability and Reversible Redox‐Proaromatic Character towards  Carbo ‐Benzenes | Zendy

Cocq Kévin | Zendy; Maraval Valérie | Zendy; SaffonMerceron Nathalie | Zendy; Saquet Alix | Zendy; Poidevin Corentin | Zendy; Lepetit Christine | Zendy; Chauvin Remi | Zendy

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

Author(s) -

Cocq Kévin,

Maraval Valérie,

SaffonMerceron Nathalie,

Saquet Alix,

Poidevin Corentin,

Lepetit Christine,

Chauvin Remi

Publication year - 2015

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201407889

Subject(s) - hydroquinone , chemistry , benzene , redox , benzoquinone , derivative (finance) , medicinal chemistry , quinone , ring (chemistry) , benzene derivatives , alkoxy group , photochemistry , stereochemistry , organic chemistry , chemical synthesis , alkyl , biochemistry , financial economics , economics , in vitro

The carbo‐mer of the para‐quinodimethane core is stable within in a bis(9‐fluorenylidene) derivative. Oxidation of this carbo‐quinoid with MnO 2 in the presence of SnCl 2 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 SnCl 2 , 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).

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