Trimethylenemethane Palladium Catalysed Cycloadditions Step 2

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

^{Click the structures and reaction black arrows in sequence to view the 3D models and animations respectively}
In these animations, the R group is represented as a purple hydrogen. The mechanism is thought to be stepwise whereby the carbanion undergoes a conjugate addition reaction with cyclopentanone. This is followed by an attack on the Pi-allyl palladium unit by the formed enolate. The resulting product from this overall ‘cycloaddition’ has an exomethylene group.

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