Asymmetric anionic polymerization of maleimide bearing an N-4 '-benzo 15-crown-5 ether with an organometal/chiral ligand complex

作者：Azechi Motohisa; Yamabuki Kazuhiro; Onimura Kenjiro; Oishi Tsutomu^*

来源：Polymer Journal, 2010, 42(8): 632-639.

DOI：10.1038/pj.2010.54

• anionic polymerization
• asymmetric polymerization
• crown ether
• maleimide

Asymmetric anionic homopolymerization of N-4'-benzo 15-crown-5 maleimide (B15C5MI) was carried out with a chiral anionic initiator consisting of organometal (n-butyllithium, diethylzinc (Et(2)Zn)) and chiral ligand ((-)-sparteine ((-)-Sp), (S, S)-(1-ethylpropylidene)-bis(4-benzyl-2-oxazoline) ((S, S)-Bnbox)) to obtain optically active polymers. The polymer obtained with the chiral ligand had an optical rotation, suggesting that asymmetric induction occurred on the main chain of the polymer. Poly(B15C5MI) obtained with Et(2)Zn/(S, S)-Bnbox in tetrahydrofuran showed the highest specific rotation of 64.1 degrees. The chiroptical properties and structures of the polymers obtained were analyzed by circular dichroism, ultraviolet, nuclear magnetic resonance and gel permeation chromatography measurements. The effects of adding (R)-cyclohexylethylamine to the obtained poly(B15C5MI) were investigated. Polymer Journal (2010) 42, 632-639; doi:10.1038/pj.2010.54; published online 30 June 2010

• 出版日期2010-8