Organopalladium Chemistry

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Trimethylenemethane Palladium Catalysed Cycloadditions

NOTE: Important charges and non-bonding electrons are shown throughout the animation except during the transition state phase.

This reaction produces a zwitterionic palladium trimethylenemethane complex that can successfully undergo cycloaddition reactions which can prove powerful in producing different five membered rings. Formation of this palladium pi-allyl complex is followed by the removal of the trimethylsilyl group by nucleophilic attack of the acetate ion.

Click the structures and reaction black arrows in sequence to view the 3D models and animations respectively

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B. M. Trost, J. P. Stambuli, S. M. Silverman and U. Schwörer, J. Am. Chem. Soc., 2006, 128, 13328–13329.