On the syntheses of dibenzosuberenone and 2,8-dimethyl-dibenzosuberenone

Abstract

Catalytic dehydrogenation of dibenzosuberone to dibenzosuberenone was performed upon microwave irradiation. Although high yields could be obtained after a short reaction time of 30 minutes for unsubstituted dibenzosuberone, the procedure unexpectedly failed if 2,8-dimethyldibenzosuberone was used as a reactant. An alternative method for the preparation of 2,8- dimethyldibenzosuberenone involving radical bromination with 2,2′-azo-bis-isobutyronitrile (AIBN) and dehydrohalogenation under basic conditions was thus applied to obtain the target compound.