Origins of boat or chair preferences in the Ireland-Claisen rearrangements of cyclohexenyl esters: A theoretical study

被引:38
作者
Khaledy, MM
Kalani, MYS
Khuong, KS
Houk, KN
Aviyente, V
Neier, R
Soldermann, N
Velker, J
机构
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
[2] Bogazici Univ, Dept Chem, TR-80815 Istanbul, Turkey
[3] Univ Neuchatel, Dept Chem, CH-2000 Neuchatel, Switzerland
关键词
D O I
10.1021/jo020595b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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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页码:572 / 577
页数:6
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