Origins of boat or chair preferences in the Ireland-Claisen rearrangements of cyclohexenyl esters: a theoretical study.
The relative energies of the chair and boat transition states of a variety of Ireland-Claisen rearrangements were obtained by B3LYP/6-31G calculations. Theoretical results are in good agreement with experimental data and provide a quantitative analysis of the origins of boat preferences that are observed in some of these reactions.
Khaledy
Mahmood M
MM
Chemistry Department, University of Neuchatel, Av. De Bellavaux 51, Switzerland.
Kalani
Mohammad Y S
MY
Khuong
Kelli S
KS
Houk
K N
KN
Aviyente
Viktorya
V
Neier
Reinhard
R
Soldermann
Nicolas
N
Velker
Joerg
J
D003510:Cyclohexanes / Q000032:analysis* / Q000737:chemistry*; D004952:Esters / Q000032:analysis / Q000737:chemistry; D008962:Models, Theoretical; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D003510:Cyclohexanes; D004952:Esters