Water-soluble poly(4,7,10,13-tetraoxatetradecylmethylsilane): enhanced yield and improved purity via polymerization using graphite-potassium (C8K) as reducing agent

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Thomas J. Cleij, Stellar K. Y. Tsang and Leonardus W. Jenneskens


Abstract

Application of graphite-potassium (C8K, THF, 0 °C), instead of convential Wurtz-type coupling conditions (Na, toluene, 110 °C), as reducing agent for the preparation of non-ionic, watersoluble poly(4,7,10,13-tetraoxatetradecylmethylsilane) 1 gives a markedly enhanced yield as well as a high molecular weight polymer of high purity.


References

  1. For a review: R. D. Miller and J. Michl, Chem. Rev., 1989, 89, 1359 Search PubMed.
  2. For a review: S. Hayase, CHEMTECH, 1994, October 19 and references cited therein.
  3. T. Seki, A. Tohnai, T. Tamaki and K. Ueno, J. Chem. Soc., Chem. Commun., 1993, 1876 RSC; T. Seki, N. Tanigaki, K. Yase, A. Kaito, T. Tamaki, K. Ueno and Y. Tanaka, Macromolecules, 1995, 28, 5609 CrossRef CAS.
  4. J. S. Hrkach and K. Matyjaszewski, Macromolecules, 1990, 23, 4042 CrossRef CAS; K. Matyjaszewski, J. S. Hrkach, H.-K. Kim and K. Ruehl, in Silicon Based Polymer Science: A Comprehensive Resource, ed. J. M. Ziegler and F. W. Gordon Fearon, Advances in Chemistry Series 224, ACS, Washington DC, 1990 Search PubMed.
  5. C. H. Yuan and R. West, Macromolecules, 1993, 26, 2645 CrossRef CAS; H. Frey, G. J. J. Out, M. Möller, D. Greszta and K. Matyjaszewski, Macromolecules, 1993, 26, 6231 CrossRef CAS; J. S. Hrkach and K. Matyjaszewski, J. Polym. Sci. Part A: Polym. Chem., 1994, 32, 1949 CrossRef CAS.
  6. C. A. van Walree, T. J. Cleij, J. W. Zwikker and L. W. Jenneskens, Macromolecules, 1995, 28, 8696 CrossRef CAS.
  7. K. Oka, N. Fujiue, S. Nakanishi, T. Takata, T. Dohmaru, C.-H. Yuan and R. West, Chem. Lett., 1995, 875 CAS.
  8. T. Seki, A. Tohnai, T. Tamaki and A. Kaito, Macromolecules, 1996, 29, 4813 CrossRef CAS; T. Seki, A. Tohnai, T. Tamaki and A. Kaito, Chem. Lett., 1996, 361 CAS; M. Yoshida, T. Seki, F. Nakanishi, K. Sakamoto and H. Sakurai, Chem. Commun., 1996, 1381 RSC.
  9. A. Fürstner and H. Weidman, J. Organomet. Chem., 1988, 354, 15 CrossRef; R. Csuk, B. I. Gläanzer and A. Fürstner, Adv. Organomet. Chem., 1988, 28, 85 CAS; A. Fürstner, Angew. Chem., Int. Ed. Engl., 1993, 32, 164 CrossRef.
  10. B. Lacave-Goffin, L. Hevesi and J. Devaux, J. Chem. Soc., Chem. Commun., 1995, 769 RSC; R. G. Jones, R. E. Benfield, P. J. Evans and A. C. Swain, J. Chem. Soc., Chem. Commun., 1995, 1465 RSC.
  11. W. Uhlig, Z. Naturforsch., 1995, 50b, 1674 Search PubMed and references cited therein.
  12. E. A. Williams and J. D. Cargioli, in Annual Reports on NMR Spectroscopy, ed. G. A. Webb, Academic Press, 1979, vol. 9, p. 221 Search PubMed.
  13. B. Lacave-Goffin, J. Devaux and L. Hevesi, XIth International Symposium on Organosilicon Chemistry, Montpellier, France, Sept. 1–6, 1996; abstract OC16 Search PubMed.
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