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Updated: Jul 17, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Tandem Oxidative Dearomatizations of Diphenylanthracene Atropisomers
Mattéo Cayla1, Dorian Sonet1, Emilien Tarayre1
1Univ. Bordeaux, CNRS, Bordeaux INP, ISM, UMR 5255, F-33400 Talence, France.
Abstract:
The first examples of tandem oxidative dearomatizations of 9,10-diphenylanthracene atropisomers with ortho,ortho'- formyl substituents are presented. In the presence of KMnO4, their stereoselective tandem double oxidation and spirocyclization mainly afford the syn or anti dearomatized 9,10-diphthalide anthracenes. Using Pinnick's reagent and depending on the conditions, the oxidation can mainly lead to the corresponding syn or anti diacids in good yields or to three oxidation products. An unprecedented further oxidative ring expansion toward dibenzo[b,e]oxepines is also reported.
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