Abstract
Zwitterionic intermediates play a crucial role in the [2 + 2] cycloaddition reaction between thioketene and formaldimine to give 2-thioazetidinone (depicted on the right), for which HF, MP 2, B 3 LYP, and HF SCRF calculations predict conrotatory ring closure to be the rate-determining step. The reaction rate is not sensitive to solvent polarity, and electronic effects of substituents are more important than the steric effects.
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