Living Anionic Polymerization of N-Methacryloylazetidine: Anionic Polymerizability of N,N-Dialkylmethacrylamides
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Abstract
Anionic polymerization of a series of N,N-dialkylmethacrylamides such as N-methacryloylazetidine (M4), N-methacryloylpyrrolidine (M5), and N-methacryloylpiperidine (M6) was carried out with diphenylmethyllithium (Ph2CHLi) or diphenylmethylpotassium (Ph2CHK) in the presence of LiCl or Et2Zn in THF to clarify the relationship between polymerizability and monomer structure. Poly(M4)s possessing predicted molecular weights and very narrow molecular weight distributions (Mw/Mn M4 > M5 ≫ M6 = DMMA). The observed relative polymerizability was well correlated with the chemical shifts of vinyl β-carbons for monomers in the 13C NMR spectra. The NMR data suggested that the polymerizable M3 and M4 attained effective conjugation between C═C and C═O double bonds, while M5, M6, and DMMA had negligible conjugation effects.
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