ELECTROSTATIC SOLVENT EFFECT ON THE KETENE-IMINE CYCLOADDITION REACTION

The ketene + formaldimine cycloaddition reaction to give 2-azetidinone has been studied as a model of one of the most interesting methods fo r the synthesis of beta-lactams. The role of the solvent has been anal yzed using a self-consistent reaction field method in which the solvat ion energy is obtained using a multipole expansion of the molecular ch arge distribution. Substantial solvent effects are predicted both for the reaction mechanism and for the reaction rate. Zero-point energy co rrections have been shown to also be important.