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

J Org Chem. 2003 Jan 24;68(2):572-7. doi: 10.1021/jo020595b.

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 types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Cyclohexanes / analysis*
  • Cyclohexanes / chemistry*
  • Esters / analysis
  • Esters / chemistry
  • Models, Theoretical*
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism

Substances

  • Cyclohexanes
  • Esters