Advertisement

Ring-opening metathesis polymerization of cyclic alkenes

  • A. J. Amass

Abstract

The ring-opening polymerization of cyclic alkenes is a special case of the more general olefin metathesis reaction. A number of specialist reviews1 have appeared in the literature on both the metathesis of alkenes and ring-opening polymerization. The metathesis reaction was initially discovered by Banks and Bailey2 but it was Calderon3 who first recognized the relationship between ring-opening polymerization and the olefin metathesis, or disproportionation, reaction. The reaction is catalysed by complexes derived principally from group VI metal compounds but group IV and V compounds have also been used. Effective catalysts may be either homogeneous or heterogeneous and, although not essential as part of the catalyst system, organometallic compounds, usually either organometallic aluminium or tin compounds, are incorporated as a second component of two component catalyst systems.

Keywords

Polymer Synthesis Transition Metal Atom Cyclic Alkene Metathesis Reaction Cyclic Oligomer 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Ivin, K.J.: Olefin Metathesis, Academic Press, London (1983);Google Scholar
  2. Dragutan, V., Balaban, A.T. and Dimonie, M.: Olefin Metathesis and Ring Opening Polymerization of Cyclo-olefins(2nd. edn), Wiley-Interscience, New York (1985).Google Scholar
  3. Rooney, J.J. and Steward, A.: Chem. Soc. Specialist Periodical Reports, Catalysis 1, 277 (1977).Google Scholar
  4. 2.
    Banks, R.L., and Bailey, G.C.: Ind. Eng. Chem. Prod. Res. Dey. 3, 170 (1964).CrossRefGoogle Scholar
  5. 3.
    Calderon, N., Chen, N.Y. and Scott, K.W.,: Tetrahedron Letters 34, 3327 (1967).CrossRefGoogle Scholar
  6. 4.
    Edwards, J.H. and Feast, W.J.: Polymer 21, 595 (1980).CrossRefGoogle Scholar
  7. 5.
    Patton, P.A. and McCarthy, T.J.: Macromolecules 20, 778 (1987).CrossRefGoogle Scholar
  8. 6.
    Feast, W.J. and Wilson, B.: J. Molec. Catal. 8, 277 (1980).CrossRefGoogle Scholar
  9. 7.
    Pampus, G., Witte, J. and Hoffmann, M.: Rev. Gen. Caout. Plast. 47, 1343 (1970).Google Scholar
  10. 8.
    Reif, L. and Hoecker, H.: Makromol. Chem., Rapid Commun. 2, 745 (1981).CrossRefGoogle Scholar
  11. 9.
    Boelhouwer, C. and Mol, C.J.: Prog. Lipid Res. 24, 243 (1985).CrossRefGoogle Scholar
  12. 10.
    Amass, A.J., Dale, A.L. and Tighe, B.J.: Makromol. Chem. 189, 515 (1988).CrossRefGoogle Scholar
  13. 11.
    Novak, B.M. and Grubbs, R.H.: J. Amer. Chem. Soc., 110, 960 (1988).CrossRefGoogle Scholar
  14. 12.
    Schrock, R.R., Grubbs, R.H., Feldman, J. and Cannizzo, L.F.: Macromolecules 20, 1169 (1987).CrossRefGoogle Scholar
  15. 13.
    Eleuterio H.S.: US Patent (1957) 3074918Google Scholar
  16. Eleuterio H.S.: Chem. Abstr. 55, 16005 (1961).Google Scholar
  17. 14.
    Verkuijlen, E., Kapteijn, F., Mol, J.C. and Boelhouwer, C.: J. Chem. Soc., Chem. Commun.198 (1977).Google Scholar
  18. 15.
    Amass, A.J. and McGourtey, T.A.: Eur. Polym. J. 16, 235 (1980).CrossRefGoogle Scholar
  19. 16.
    Schrock, R.R., Krouse, S.A., Knoll, K., Feldman, J., Murdzek, J.S. and Yang, D.C.: J. Mol. Cat. 46, 243 (1988).CrossRefGoogle Scholar
  20. 17.
    Wallace, K.R., Liu, A.H., Dewan J.C. and Schrock, R.R.: J. Amer. Chem. Soc. 110, 4964 (1988).CrossRefGoogle Scholar
  21. 18.
    Gilliom, L.R. and Grubbs, R.H.: J. Amer. Chem. Soc. 108, 733 (1986).CrossRefGoogle Scholar
  22. 19.
    Farona, M.F., Lofgren, P.A. and Woon, P.S.: J. Chem. Soc., Chem. Comm.246 (1974).Google Scholar
  23. 20.
    Guenther, P., Haas, F., Marwede, G., Nuetzel, K., Oberkirch, W., Pampus, G., Schoen, N. and Witte, J.: Angew. Makromol. Chem. 14, 87 (1970).CrossRefGoogle Scholar
  24. 21.
    Wallace, K.R. and Schrock, R.R.: Macromolecules 20, 448 (1987).CrossRefGoogle Scholar
  25. 22.
    Natta, G., Dall’Asta, G. and Motroni, G.: J. Polym Sci. Polym. Lett. B2, 349 (1964).CrossRefGoogle Scholar
  26. 23.
    Michelotti, F.W. and Keaveney, W.P.: J. Polym Sci. A3, 895 (1965).Google Scholar
  27. 24.
    Ivin, K.J., Laverty, D.T., O’Donnell, J.H., Rooney, J.J. and Stewart, C.D.: Makromol. Chem. 180, 1989 (1979).CrossRefGoogle Scholar
  28. 25.
    Natta, G., Dall-Asta, G., Mazzanti, G. and Motroni, G.: Makromol. Chem. 69, 163 (1963).CrossRefGoogle Scholar
  29. 26.
    Calderon, N., Ofstead, E.A. and Judy, W.A.: J. Polym Sci. A(1), 5, 2209 (1967).Google Scholar
  30. 27.
    Dall’Asta, G. and Montroni, G.: Chem. Abstr. 66, 19005 (1967).Google Scholar
  31. 28.
    Katz, T. J. and Acton, N.: Tetrahedron Letters4251 (1976).Google Scholar
  32. 29.
    Katz, T.J., Lee, S. J. and Acton, N.: Tetrahedron Letters4247 (1976).Google Scholar
  33. 30.
    Katz, T.J., Lee S.J. and Shippey, M.A.: J. Mol. Catal. 8, 219 (1980).CrossRefGoogle Scholar
  34. 31.
    Kress, J., Osborne, J.A., Green, R.M.E., Ivin, K.J., Rooney, J.J.: J. Chem. Soc., Chem. Commun.874 (1985).Google Scholar
  35. 32.
    Kress, J. and Osborne, J.A.: J. Amer. Chem. Soc. 109, 3953 (1987).CrossRefGoogle Scholar
  36. 33.
    Kress, J., Osborne, J.A., Green, R.M.E., Ivin, K.J. and Rooney, J.J.: J. Amer. Chem. Soc. 109, 899 (1987).CrossRefGoogle Scholar
  37. 34.
    Kress, J., Osborne, J.A., Amir-Ebrahimi, V., Ivin, K.J. and Rooney, J.J.: J. Chem. Soc., Chem. Comm.1164 (1988).Google Scholar
  38. 35.
    Amass, A.J. and Gregory D.: Brit. Polym J. 19, 263 (1987).Google Scholar
  39. 36.
    Calderon, N., Ofstead, E.A., Ward, J.P., Judy, W.A. and Scott, K.W.: J. Amer. Chem. Soc. 90, 4133 (1968).CrossRefGoogle Scholar
  40. 37.
    Dall’Asta, G. and Montroni, G.: Eur. Polym. J. 7, 707 (1971).CrossRefGoogle Scholar
  41. 38.
    Mango, F.D. and Schachtschneider, J.H.: J. Amer. Chem. Soc. 93, 1123 (1971).CrossRefGoogle Scholar
  42. 39.
    Lewandos, G.S. and Pettit, R. Tetrahedron Letters789 (1971).Google Scholar
  43. 40.
    Biefield, C.G., Eick, H.A. and Grubbs, R.H.: Lnorg. Chem. 12, 2166 (1973).CrossRefGoogle Scholar
  44. 41.
    Herisson, J.L. and Chauvin, Y.: Makromol. Chem. 141, 161 (1970).CrossRefGoogle Scholar
  45. 42.
    Katz, T.J. and McGinnis J.: J. Amer. Chem. Soc. 97, 1592 (1975).CrossRefGoogle Scholar
  46. 43.
    Casey, C.P. and Shusterman, A.J.: J. Molec. Catal. 8, 1 (1980).CrossRefGoogle Scholar
  47. 44.
    Casey, C.P., Tuinstra, H.E. and Saeman, M.C.: J. Amer. Chem. Soc. 98, 608 (1976).CrossRefGoogle Scholar
  48. 45.
    Schrock, R.R., Rocklage, S., Wengrovius, J., Rupprecht, G. and Feldman, J.: J. Molec. Catal. 8, 73 (1980).CrossRefGoogle Scholar
  49. 46.
    Amass, A.J. and Zurimendi, J.A.: Eur. Polym. J. 17, 1 (1981).CrossRefGoogle Scholar
  50. 47.
    Tebbe, F.N., Parshall, G.W. and Reddy, G.: J. Amer. Chem. Soc. 100, 3611 (1978).CrossRefGoogle Scholar
  51. 48.
    Howard, T.R., Lee, J.B. and Grubbs, R.H.: J. Amer. Chem. Soc. 102, 6876 (1980).CrossRefGoogle Scholar
  52. 49.
    Ott, K.C., Lee, J.B. and Grubbs, R.H.: J. Amer. Chem. Soc. 104, 2942 (1982).CrossRefGoogle Scholar
  53. 50.
    Wengrovius, J.H., Schrock, R.R., Churchill, M.R., Missert, J.R. and Youngs, W.J.: J. Amer. Chem. Soc. 102, 4515 (1980).CrossRefGoogle Scholar
  54. 51.
    Murdzek J.S. and Schrock, R.R. Macromolecules 20(1987).Google Scholar
  55. 52.
    Knoll, K., Krouse, S.A. and Schrock, R.R.: J. Amer. Chem. Soc. 110, 4424 (1988).CrossRefGoogle Scholar
  56. 53.
    Pampus, G., Witte J. and Hoffmann, M.: Rev. Gen. Caout. Plast. 47, 1343 (1970).Google Scholar
  57. 54.
    Amass, A.J. and McGourtey, T.A.: Proceedings of ‘Catalyse par Coordination (Villeurbanne, Lyon, France)’p. 181 (1974).Google Scholar
  58. 55.
    Hoecker, H., Reiman, W., Reif L. and Riebel K.: Rec. Tray. Chim. Pays-Bas 96, M47 (1977).Google Scholar
  59. 56.
    Amass, A.J. and Zurimendi, J.A.: Polymer 23, 211 (1982).CrossRefGoogle Scholar
  60. 57.
    Amass, A.J. and Tuck C.N.: Eur. Polym. J. 14, 817 (1978).CrossRefGoogle Scholar
  61. 58.
    Ivin, K.J., O’Donnell, J.H., Rooney, J.J. and Stewart, C.D.: Makromol. Chem. 180, 1975 (1979).CrossRefGoogle Scholar
  62. 59.
    Ivin, K.J., Lapiensis, G., Rooney, J.J. and Stewart, C.D.: J. Molec. Catal. 8, 203 (1980)CrossRefGoogle Scholar
  63. 60.
    Green, R.M.E., Hamilton, J.G., Ivin, K.J. and Rooney, J.J.: Makromol. Chem. 187, 619 (1986).CrossRefGoogle Scholar
  64. 61.
    Ho, H.T., Reddy, B.S.R. and Rooney, J.J.: J. Chem. Soc., Faraday Trans 1. 78, 3307 (1982).CrossRefGoogle Scholar
  65. 62.
    Dainton, F.S. and Ivin, K.J.: Quart. Rev. 12, 61 (1958).CrossRefGoogle Scholar

Copyright information

© Blackie & Son Ltd. 1991

Authors and Affiliations

  • A. J. Amass

There are no affiliations available

Personalised recommendations