OBSERVATION OF A COMPETITIVE PATH IN THE NUCLEOPHILIC ADDITION OF FLUOROOLEFINS: THE BROMOPHILIC REACTION OF THE ADDUCT CARBANOIN INTERMEDIATE

Article abstract of DOI:10.1016/S0022-1139(00)81976-4

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 bromotrifluoro-ethene (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.