a-(Trifluoromethyl)styrene (Q = 0.43, e = 0.90) does not undergo radical homopolymerization. Anionic polymerization fails to produce appreciable amounts of polymer even in bulk at -78 °C in spite of its high e value. The resistance to anionic polymerization is primarily due to side reactions involving addition-elimination sequences (Sn2') when initiators are nucleophilic enough to add to the 3-carbon of TFMST. Weaker anionic initiators such as pyridine and potassium terf-butoxide that effectively induce polymerization of methyl a-(trifluoromethyl)acrylate (Q = 0.74, e = 2.5) do not react with TFMST. Reactions of TFMST with several anionic initiators are described in detail.
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