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.