Studies on the Configurational Stability of Tropolone-Ketone-, Ester-, and Aldehyde-Based Chiral Axes.
J Org Chem
; 89(1): 541-552, 2024 Jan 05.
Article
en En
| MEDLINE
| ID: mdl-38133833
ABSTRACT
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.
Texto completo:
1
Bases de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2024
Tipo del documento:
Article
País de afiliación:
Estados Unidos