Electronic structure and kinetic behavior of 4-(cycloheptatrienylidene)cyclohexa-2,5-dienone (or [6.7]Quinaren-9-one) and its derivatives)

The conjugative interaction between the two terminal groups in title quinarenone 2 and its chloro- and methoxy-derivatives were evaluated, proving that the diatropicity of the seven-membered ring is a little larger in 2 than in tropone. Some of these quinarenones are also found to exist in equilibrium with their oligomers and show unexpectedly low barriers of rotation about the intercyclic bond.