Abstract
The anionic polymerization of 5-(N,N-dialkylamino)isoprenes carrying various alkyl substituents was studied in nonpolar (benzene, hexane) and polar solvents (tetrahydrofuran, dioxane, triethylamine). The microstructure is found to be strongly dependent on the bulkiness of the tertiary amino group. All polymerizations in nonpolar solvents occur by a 4,1-addition of the monomer to the anionic chain end. In THF no polymerization occurs. The results are discussed with respect to the stereoelectronic situation at the growing chain end. For monomers with the most bully branched side groups (isopropyl, isobutyl, and 2,6-cis-dimethylpiperidyl) the addition is not only regioselective but also stereoselective, giving rise to the formation of stereoregular polymers with cis-4,1-repeating units
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