The mechanism to form fluoroalkene products from defluoroalkylation of HCF3 is clearly complex. It requires a 2:1 reaction stoichiometry of organolithium:HCF3 and elimination of two equiv. of lithium fluoride. Moreover, the product forms as a single constitutional isomer with both fluorine and silyl substituents connected to the same carbon atom. Keen to understand this process further we sought to model potential reaction pathways through computational methods.