Tandem Oxidative Dearomatizations of Diphenylanthracene Atropisomers.

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.

Citation

Mattéo Cayla, Dorian Sonet, Emilien Tarayre, Romain Bapt, Brigitte Bibal. Tandem Oxidative Dearomatizations of Diphenylanthracene Atropisomers. The Journal of organic chemistry. 2023 Sep 15;88(18):13067-13075

PMID: 37673031

search → result