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  Home > JCE Print > Journal of Chemical Education > Issues > 1997  > May  >
In the Laboratory
endo- and exo-Stereochemistry in the Diels-Alder Reaction: Kinetic versus Thermodynamic Control
James H. Cooley and Richard Vaughan Williams
Department of Chemistry, University of Idaho, Moscow, ID 83844-2343
Cover
May 1997
Vol. 74 No. 5
p. 582
Abstract
In these experiments, which were used in the problem-solving mode, the stereoselectivity of the Diels-Alder cycloaddition of N-phenylmaleimide to furan is deduced by the characteristic splitting patterns in the proton-NMR spectra. The relationship of coupling constants to dihedral angle, as described by the Karplus equation, is illustrated. The data can also be used to demonstrate the concept of kinetic versus thermodynamic control.
More Information
*  Citation
 Cooley, James H.; Williams, Richard Vaughan. J. Chem. Educ. 1997 74 582.
*  Keywords
 Laboratory Instruction, Organic Chemistry, Kinetics, Molecular Modeling/Dynamics, NMR Spectrometry, Stereochemistry, Thermodynamics
*  History
 Created:
Last Updated:		 July 28, 1999
June 23, 2005
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