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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).