Structure and Reactivity of the Magnesium Alkyl–2-Alkoxyethanol System as an Initiator for Styrene Polymerization

Polymer Journal volume 4, pages421–425(1973)Cite this article

Abstract

The structure and reactivity of dialkylmagnesium–2-alkoxyethanol system as an initiator for styrene polymerization were studied. Dialkylmagnesium coupled with an equimolar quantity of 2-alkoxyethanol was found to initiate styrene polymerization, although the use of dialkylmagnesium alone could not induce polymerization. Metalation reaction of fluorene and addition reaction to 1, 1-diphenylethylene were possible with dialkylmagnesium–2-alkoxyethanol system. Measurements of the electronic spectra of these carbanion solutions indicated that coordination-agentseparated ion pairs were produced in the system. The colorless prism crystal, which was formed in di-n-butylmagnesium–2-methoxyethanol system, was found to possess a composition such as n-C4H9MgOCH2OCH3·OCH3·Mg(OCH2CH2OCH3)2. This complex exhibited high reactivity for styrene polymerization.

Download PDF

References

  1. 1

    T. Narita, A. Masaki, and T. Tsuruta, J. Macromol. Sci., Chem., A4, 277 (1970).

  2. 2

    T. Narita and T. Tsuruta, J. Organometal. Chem., 30, 289 (1971).

  3. 3

    K. H. Wong, G. Konizer, and J. Smid, J. Am. Chem. Soc., 92, 666 (1970).

  4. 4

    U. Takaki, T. H. Hogen-Esch, and J. Smid, J. Am. Chem. Soc., 93, 6760 (1971).

  5. 5

    C. F. H. Allen and S. Converse, “Organic Syntheses,” Vol. 1, John Wiley & Sons, Inc., New York, N.Y., 1941, p 226.

    Google Scholar 

  6. 6

    D. L. Cottle and W. C. Hollyday, Jr., J. Org. Chem., 12, 510 (1947).

  7. 7

    U. S. Patent 3347912 (1967).

  8. 8

    M. Tomoi and H. Kakiuchi, Kogyo Kagaku Zasshi (J. Chem. Soc. Japan, Ind. Chem. Sect.), 73, 2367 (1970).

  9. 9

    T. H. Hogen-Esch and J. Smid, J. Am. Chem. Soc., 87, 669 (1965).

  10. 10

    T. H. Hogen-Esch and J. Smid, J. Am. Chem. Soc., 88, 307 (1966).

  11. 11

    L. L. Chan and J. Smid, J. Am. Chem. Soc., 89, 4547 (1967).

  12. 12

    L. L. Chan and J. Smid, J. Am. Chem. Soc., 90, 4654 (1968).

  13. 13

    R. Waack and M. A. Doran, J. Organometal. Chem., 29, 329 (1971).

Download references

Author information

Affiliations

  1. Department of Synthetic Chemistry, Faculty of Engineering, The University of Tokyo

    Tadashi Narita, Takashi Yasumura & Teiji Tsuruta

Authors
  1. Tadashi Narita
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Takashi Yasumura
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Teiji Tsuruta
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Narita, T., Yasumura, T. & Tsuruta, T. Structure and Reactivity of the Magnesium Alkyl–2-Alkoxyethanol System as an Initiator for Styrene Polymerization. Polym J 4, 421–425 (1973). https://doi.org/10.1295/polymj.4.421

Download citation

Keywords

  • Polymerization
  • Styrene
  • Dialkylmagnesium
  • 2-Methoxyethanol
  • Tetrahydrofurfuryl Alcohol
  • Fluorene
  • 1, 1-Diphenylethylene
  • Coordination-Agent-Separated Ion Pair

Further reading

Search

Quick links