Carbo‐Quinoids: Stability and Reversible Redox‐Proaromatic Character towards Carbo‐Benzenes1. (21st January 2015)

• Record Type: Journal Article
• Authors: Cocq, Kévin; Maraval, Valérie; Saffon‐Merceron, Nathalie; Saquet, Alix; Poidevin, Corentin; Lepetit, Christine; Chauvin, Remi
• Is Part Of: Angewandte Chemie. Volume 127:Number 9(2015)
• Page Start: 2741
• Page End: 2744
• Publication Date: 2015-01-21
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201407889
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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).</p> </abstract>