Reaction of Perfluoroalkanesulfinates with Allyl and Propargyl Halides. A Convenient Synthesis of 3-(Perfluoroalkyl)prop-1-enes and 3-(Perfluoroalkyl)allenes

Article abstract of DOI:10.1021/jo00008a041

The reaction of perfluoroalkanesulfinates, R_fCF2SO2Na, with allyl and propargyl halides, in the presence of (NH4)2S2O8, gave 3-(perfluoroalkyl)prop-1-enes (R_fCH2CH=CH2) and 3-(perfluoroalkyl)allenes (R_fCH=C=CH2), respectively, in good yield.Evidence is presented for a radical addition-elimination mechanism for the reaction.The reaction represents a synthetically viable and convenient route to such compounds.