Origins of boat or chair preferences in the Ireland-Claisen rearrangements of cyclohexenyl esters: A theoretical study
Author(s)
Khaledy, Mahmood
Kalani, Mohammad
Khuong, Kelli
Houk, K. N
Aviyente, Viktorya
Soldermann, Nicolas
Velker, Joerg
Date issued
2003
In
Journal of Organic Chemistry
Vol
2
No
68
From page
572
To page
577
Subjects
COPE BICYCLOHEXANE INVERSION KINETICS CLEAVAGE
Abstract
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.
Publication type
journal article