Journal
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
Volume 55, Issue 6, Pages 1048-1058Publisher
WILEY
DOI: 10.1002/pola.28465
Keywords
anionic polymerization; stereospecific polymers; quinone methide; substituent effect; synthesis
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology, Japan [18350062, 22550110]
- Grants-in-Aid for Scientific Research [18350062, 15K05518, 22550110] Funding Source: KAKEN
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7-(o-Substituted phenyl)-2,6-dimethyl-1,4-benzoquinone methides which have an electron-donating methoxy-(oOMe, 2a) and methyl-(o-Me, 2b) substituents or an electronwithdrawing cyano- (o-CN, 2c) and trifluoromethyl- (o-CF3, 2d) substituents at the ortho-position of the aromatic ring and 7-(msubstituted phenyl)-2,6-dimethyl-1,4-benzoquinone methide with an electron-withdrawing trifluoromethyl- (m-CF3, 2e) substituent at the meta-position of the aromatic ring were synthesized, and their asymmetric anionic polymerizations using the complex of lithium 4-isopropylphenoxide with (-)-sparteine were carried out in toluene at 0 degrees C. The polymers with negative optical activity were obtained for all of five monomers, and their specific rotation values largely changed depending upon the substituents of the monomers. On the basis of the comparison of various substituents effects, it was found that the specific rotation of obtained polymers is significantly affected by the electronic effects such as inductive and resonance effects rather than the steric and electrostatic effects of the substituent. (C) 2017 Wiley Periodicals, Inc.
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