A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions

Abstract

Treatment of benzanthrone (1) with biphenyl-2-yl lithium leads to the surprisingly stable enol 4, which is converted by dehydrogenation into the benzanthrone derivative 7. Under acidic conditions 4 isomerises to the spiro compound 11 and the bicyclo[4.3.1]decane derivative 12. Furthermore, the formation of 7 and the hydrogenated compound 13 is observed. A mechanism for the formation of the reaction products is proposed and supported by DFT calculations.

Keywords

• consecutive reactions
• intramolecular cyclization
• molecular modelling
• spiro compounds
• X-ray structural analysis