Abstract
endo– exo Selectivity in Diels–Alder cycloadditions of several o-quinodimethanes ( 1– 4) with acrylonitrile, 2-(5H)-furanone and N-methylmaleimide has been investigated in acetonitrile solution. Transition structures of the cycloaddition of the parent o-QDM ( 1), ( E, E)-1,8-dimethyl- o-QDM ( 2), isoindene ( 3) and 2,3-dihydronaphthalene ( 4) with acrylonitrile and maleimide were located at both HF/6-31G∗ and B3LYP/6-31G∗ methods. Theoretical data reproduce fairly well both experimental absolute reaction rates and diastereoisomer ratios. The high endo selectivity has been rationalized mainly as a result of solvation effects (acetonitrile, PCM model) and reactant deformations. The latter is due to steric interactions.
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