Resumen de Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide

Marsha R. Baar, Kristin Wustholz

• endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a Diels–Alder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride. This Diels–Alder reaction can be performed on macro- or miniscale, at room temperature for a week or under reflux for 2.5 hours to produce a 91% yield of a white solid that precipitates from solution and can be analyzed without further purification. Typical student results after 1.5 hours of reflux were 1.05 g (78%), mp 203.4–205.3 °C (lit. 204–206 °C). Results from IR and 1H and 13C NMR were consistent with literature values.