Endo- and exo-Stereochemistry in the Diels-Alder Reaction:: Kinetic versus Thermodynamic Control

James H. Cooley ^[1] ; Richard Vaughan Williams ^[1]
1. [1] University of Idaho
  
  University of Idaho
  
  Estados Unidos
Localización: Journal of chemical education, ISSN 0021-9584, Vol. 74, Nº 5 (May), 1997, págs. 582-585
Idioma: inglés
Texto completo no disponible (Saber más ...)
Resumen
- 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.