Origins of Boat or Chair Preferences in the Ireland−Claisen Rearrangements of Cyclohexenyl Esters: A Theoretical Study
The Journal of Organic Chemistry2002Vol. 68(2), pp. 572–577
Citations Over TimeTop 19% of 2002 papers
Mahmood M. Khaledy, M. Yashar S. Kalani, Kelli S. Khuong, K. N. Houk, Vi̇ktorya Avi̇yente, Reinhard Neier, Nicolas Soldermann, J. Velker
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.
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