Why diels-alder reactions are non-concerted processes

• LUIS R DOMINGO ^[1]
  1. [1] Universitat de València

     Universitat de València

     Valencia, España

     
• Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 59, Nº. 3, 2014, págs. 2615-2618
• Idioma: inglés
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• Resumen

  • Two exhaustive topological analyses using the Electron Localisation Function (ELF) along the non-polar Diels-Alder reactions of 1,3-butadiene [J. Phys. Chem. A107, 6014 (2003)] and cyclopentadiene [Org. Biomol. Chem. 8, 5495, (2010)] with ethylene established that the bonding changes along these reactions are non-concerted. Herein, the ELF bonding changes along the intramolecular Diels-Alder reaction of 1-(hex-5-enyl)cyclohexa-1,3-diene is analysed. The geometrical restrictions imposed by the tether break the synchronicity in the single bond formation in this non-polar reaction. The present ELF topological analysis along this intramolecular Diels-Alder reaction supports the earlier findings that established the non-concerted nature of Diels-Alder reactions.