Regioselectivity in hetero diels-alder reactions

Grosso, Carla; Liber, Marta; Brigas, Amadeu; Pinho e Melo, Teresa M. V. D.; Lemos, Americo

http://hdl.handle.net/10400.1/14489

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Authors

Grosso, Carla

Liber, Marta

Brigas, Amadeu

Pinho e Melo, Teresa M. V. D.

Lemos, Americo

Abstract(s)

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.