Observation of a Competitive Path in the Nucleophilic Addition of Fluoroolefins: The Bromophilic Reaction of the Adduct Carbanion Intermediate.

Abstract In addition to the hydro-alkoxy-addition products ROCF2CFBrH(4), and olefin products ROCFCFBr(5), a new type of product, i.e. , the alkoxy-bromo-addition products ROCF2CFBr2 (6) have been obtained in the reactions of bromotrifluoroethene(3) with different alkoxides (RO- = t-BuO-, i-PrO-, EtO- and MeO-). These products(6) are formed from a competitive path involving bromophilic reactions of the intermediate adduct carbanions(8). Radicals have been shown to be unlikely intermediates of this competitive reaction path.