Abstract
2-(6-Methylpyridyl)diphenylmethyl methacrylate (MPyDMA) was synthesized and polymerized with chiral anionic initiators, organolithium complexes of (2S,3S)-(+)-1,4-bis(dimethylamino)-2,3-dimethoxybutane (DDB) and (2S,3S)-(+)-2,3-dimethoxy-1,4-dipiperidinobutane (DPB). The obtained polymer showed a large optical rotation due to prevailing one-handed helical structure. The polymerization of MPyDMA was affected by the addition of a polar compound, piperidine but the extent was less than the polymerization of diphenyl-2-pyridylmethyl methacrylate (D2PyMA). Low-molecular-weight poly(MPyDMA) decreased its optical activity in chloroform. This may be due to a stereomutation with helix-helix transition. Optically active poly(MPyDMA) exhibited lower optical resolving power as a chiral stationary phase for HPLC than poly(D2PyMA).
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Mohri, H., Okamoto, Y. & Hatada, K. Helix-Sense-Selective Polymerization of 2-(6-Methylpyridyl)diphenylmethyl Methacrylate. Polym J 21, 719–724 (1989). https://doi.org/10.1295/polymj.21.719
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DOI: https://doi.org/10.1295/polymj.21.719