Stability of Medium-Ring Cyclic Unsaturated Carbonyl Compounds: Direct Access to Unsaturated Ketones with C–C Double Bonds at Distal Positions via Transfer Dehydrogenation of Alicyclic Ketones

Medium-ring cyclic compounds have characteristic distortions. For alicyclic enones, conjugated enones are known to be less stable than unconjugated enones. In this study, the relative stability of cycloalkenones with varied C–C double bond positions with C6–C12 rings was theoretically investigated to reveal that C8–C12 cycloalkenones prefer the unconjugated isomer. Furthermore, direct access to distal unsaturated cycloalkenones has been accomplished by transfer dehydrogenation of cycloalkanones catalyzed by iridium complexes.