Regioselectivity in Hetero Diels–Alder Reactions

Carla Grosso ^[1] ; Marta Liber ^[2] ; Amadeu F. Brigas ^[2] ; Teresa M. V. D. Pinho e Melo ^[1] ; Américo Lemos ^[1]
1. [1] Universidade de Coimbra
  
  Universidade de Coimbra
  
  Coimbra (Sé Nova), Portugal
2. [2] Universidade do Algarve
  
  Universidade do Algarve
  
  Faro (Sé), Portugal
Localización: Journal of chemical education, ISSN 0021-9584, Vol. 96, Nº 1, 2019, págs. 148-152
Idioma: inglés
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Resumen
- Regioselectivity in hetero Diels–Alder reactions can be observed in a simple reaction between a nonsymmetrical heterodiene and an unsymmetrical heterodienophile. A 9 h and easy to implement laboratory experiment is described, in which students can observe the regioselectivity of inverse “electron-demand” hetero Diels–Alder reactions of an azoalkene with furan or 2,3-dihydrofuran acting as dienophile. This experiment combines synthesis, structural analysis (IR spectroscopy and NMR spectroscopy), and dry- and vacuum-flash isolation methods.