Reaction of α-trifluoromethylstyrene with anionic initiators

The authors investigated preferred pathways in the 1:1 reaction of TFMST (alpha-trifluoromethylstyrene) with several anionic initiators. The reactions were in general much cleaner than that of MTFMA (Methyl alpha(trifluoromethyl)acryl) with nBuLi which involves participation of the ester functionality. The major common products were gem-difluoroolefins and trisubstituted fluoroethylenes. The identification of the products was achieved by comparison of GC retention times, IR, 1H, 13C, and 19F NMR spectra, elemental analysis, and GC/MS of products (isolated in many cases) with those of synthesized samples.