Density-functional theory and CASSCF calculations are usedto explore the potential energy surface of the reaction betweentetrafluoroethylene and butadiene. Unlike traditional reactions between a diene and a dienophile, thisreaction proceeds through a diradical intermediate to form the[2+2]cycloaddition product, 1,1,2,2-tetrafluoro-3-vinylcyclobutane.  The molecular dynamics of the potentialenergy curve are currently being studied, since diradicals generally have ahigh reactivity and short lifetime. The Diels-Alder pathway has also been explored to confirm that the [4+2]cycloadditionis a higher energy pathway as experimental evidence suggests.

[2+2]Cycloaddition
via diradical intermediates

239th National Meeting (2010)

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