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Chemical Physics Letters

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We examine radical mediated pathways in electrophilic addition to the simplest alkene, ethylene, where the structure of the radical intermediate has been extensively debated. Starting from the π-complex with a dihalogen, C2H4⋯I2, isolated in an inert matrix, we initiate reaction by photolytically cleaving the I2 bond. We succeed in trapping and spectroscopically interrogating the symmetrically bridged radical complex, which calculations confirm is the global minimum on the C2H5I Potential Energy Surface (PES). Consistent with the participation of a bridged intermediate, radical addition preferentially but not exclusively yields the anti-stereoisomer of the 1,2-diiodoethane product.


Accepted version. Chemical Physics Letters, Vol. 554, No. 3 (December 2012): 86–89. DOI. © 2012 Elsevier. Used with permission.

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