Looking beyond the endo Rule in a Diels-Alder Discovery Lab

• Ronald M. Jarret ^[1] ; Jamie New ^[1] ; Rebecca Hurley ^[1] ; Laura Gillooly ^[1]
  1. [1] College of the Holy Cross

     College of the Holy Cross

     City of Worcester, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 78, Nº 9, 2001, pág. 1262
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • The commonly described reaction of maleic anhydride and cyclopentadiene generates a Diels-Alder product in accord with the endo rule. Replacing the dienophile with maleic acid or fumaric acid (with modified reaction conditions) allows students to discover or verify that the Diels-Alder reaction is stereospecific with respect to the stereochemistry of the alkene. The recording of NMR spectra is a particularly useful means of establishing cis-trans stereochemistry (symmetry) of the products.