SEARCH

SEARCH BY CITATION

Keywords:

  • chiral;
  • α,β-unsaturated ketone;
  • synthesis;
  • anionic polymerization;
  • helical polymer

Abstract

((−)-Menthyl (S)-6′-acrylyl-2′-methyloxy-1,1′-binaphthalene-2-carboxylate (3) was synthesized and anionically polymerized using n-BuLi as an initiator in toluene. The monomer 3 was levorotatory and had an [α]D25 value of −72.4, but its corresponding polymer poly-3 was dextrorotatory and showed an [α]D25 value of +162.0. Poly-3 was confirmed to exist in the form of one-handed helical structure in solution by means of comparing the specific optical rotation and the CD spectra with that of 3 and the model compounds such as (−)-menthyl (S)-6′-propionyl-2′-methyloxy-1,1′-binaphthalene-2-carboxylate 2b and (−)-menthyl (S)-6′-heptanoyl-2′-methyloxy-1,1′-binaphthalene-2-carboxylate 2c. This conclusion was also confirmed by the fact that the g-value of poly-3 is about 11 times of that of monomer 3.