A novel titanium-iduced aromatic dicrbonyl coupling. Synthesis of a chiral strained polynuclear aromatic hydrocarbon
Abstract
The titanium-induced coupling of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one (3) gave 10,10′11,11′-tetrahydro-5,5′-bis(5H-dibenzo[a,d]cycloheptenyl)(5) and the chiral bridged diphenylanthracene (4), which was resolved and has a racemization barrier of ∼23 kcal/mol (1 cal = 4.184 J); the crystal structure of (4) has been determined.