Diels-Alder reaction between naphthalene and N-phenylmaleimide under ambient and high pressure conditions

Abstract

The rate and equilibrium constants for the Diels-Alder reactions between benzene and naphthalene as dienes and tetracyanoethylene, maleic anhydride and N-phenylmaleimide as dienophiles at 25°C were estimated from empirical rule. The highest yield of the adduct was predicted for the reaction of naphthalene with N-phenylmaleimide. The time of adduct formation in 50% yield exceeds 30 years. The use of gallium chloride as a catalyst affords the exo-adduct for seven days at room temperature. The rate ((2±0.5)•10-6 L mol-1 s-1) and equilibrium constants (5±2 L mol-1) of this reaction were determined. Under high pressure conditions (8kbar) reaction occurs with formation of both stereo isomers at 100°C during 80 hours. © ARKAT