Studies on the Configurational Stability of Tropolone-Ketone‑, Ester‑, and Aldehyde-Based Chiral Axes

Recent studies have revealed that tropolone-amide aryl C–C­(O) rotational barriers are dramatically higher than those of analogous benzamide-based systems, and as a result, they have an increased likelihood of displaying high configurational stability. Studies on other tropolone-based chiral axes are important to assess the generality of this phenomenon. Herein, we describe a series of studies on the rotational barriers of tropolone-ketone, tropolone-ester, and tropolone-aldehyde chiral axes. These studies are complemented with computational modeling of the dynamics of these and analogous benzenoid variants to illuminate the impact that tropolone may have on aryl–C­(O) configurational stability.