Asymmetric Polymerization and Oligomerization of 3-Phenylpropanal with Grignard Reagent−(−)-Sparteine Complexes with Termination by Tishchenko Reaction

DOI Web Site 被引用文献3件
  • Seong-Ho Choi
    Department of Applied Chemistry, School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-01, Japan
  • Eiji Yashima
    Department of Applied Chemistry, School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-01, Japan
  • Yoshio Okamoto
    Department of Applied Chemistry, School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-01, Japan

書誌事項

公開日
1996-01-01
DOI
  • 10.1021/ma951563b
公開者
American Chemical Society (ACS)

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説明

3-Phenylpropanal (3-PPA) was polymerized with Grignard reagent−(−)-sparteine complexes, such as ethylmagnesium bromide−(−)-sparteine (EtMgBr−Sp) and n-octylmagnesium bromide−(−)-sparteine (OctMgBr-SP) complexes, in toluene at low temperature. The poly(3-PPA) obtained showed optical activity with negative rotation ([α]25365 −33° to −56°), which may be based on a predominant one-handed helical conformation of the main chain, and also exhibited a signal due to an ester carbonyl group at 1738 cm-1 in its IR spectrum. This means that the polymer has an ester group at the ω-end which is formed by a Tishchenko-type termination reaction between the growing chain end and the 3-PPA monomer. The poly(3-PPA) is stable at room temperature, whereas the poly(3-PPA) obtained with EtMgBr alone at −78 °C degrades slowly even in the solid state to 3-PPA monomer at room temperature. 1H and 13C NMR spectra of the poly(3-PPA) showed rather sharp resonances, suggesting that the polymer may be stereoregular, although the tactici...

収録刊行物

  • Macromolecules

    Macromolecules 29 (6), 1880-1885, 1996-01-01

    American Chemical Society (ACS)

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