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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 °С 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 (8 kbar) reaction occurs with formation of both stereo isomers at 100 °С during 80 hours.

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