Skip to main content

Ring-opening polymerization of bicyclic and spiro compounds. Reactivities and polymerization mechanisms

  • Chapter
  • First Online:
Polymer Synthesis Oxidation Processes

Part of the book series: Advances in Polymer Science ((POLYMER,volume 102))

Abstract

Ring-opening polymerization of heterobicyclic compounds, such as bicyclic acetals, lactones, lactams, and orthoesters provides a convenient and effective route to designing functional polymers containing heterocycles in their main chains. Polycondensation and polyaddition also give some of these polymers, but ring-opening polymerization has the advantage of producing polymers not only high in molecular weight but also stereochemically regulated. The reactivity of bicyclic monomers varies over a wide range, and in addition, highly strained monomers are often ring-opened by two or more different ways. In some cases, ring-opening polymerization accompanies isomerization. These features complicate the ring-opening polymerization of bicyclic monomers. The present article reviews recent advances in ring-opening polymerization of selected bicyclic and spiro compounds, focusing on the structure-reactivity relationships and the polymerization mechanisms.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Similar content being viewed by others

9 References

  1. Hall HK Jr (1958) J Am Chem Soc 80: 6412; (1960) J Am Chem Soc 82: 1209

    Google Scholar 

  2. Okada M (to be published) Prog Polym Sci

    Google Scholar 

  3. Sumitomo H, Okada M (1978) Adv Polym Sci 28: 47

    Google Scholar 

  4. Penczek S, Kubisa P, Matyjaszewski K (1980) Adv Polym Sci 37: 1

    Google Scholar 

  5. Yokoyama Y, Hall HK Jr (1982) Adv Polym Sci 42: 107

    Google Scholar 

  6. Sumitomo H, Okada M (1984) In: Ivin K, Saegusa T (eds) Ring-opening polymerization, Elsevier, London, vol I, p 229

    Google Scholar 

  7. Penczek S, Kubisa P, Matyjaszewski K (1985) Adv Polym Sci 68/69: 1

    Google Scholar 

  8. Hall HK Jr, Fr DeBlauwe, Carr LJ, Rao VS, Reddy GS (1976) J Polym Sci Symposia No 56: 101

    Google Scholar 

  9. Deslongchamps P (1975) Tetrahedron 31: 2463

    Google Scholar 

  10. Okada M, Sumitomo H, Sumi A, Sugimoto T (1984) Macromolecules 17: 2451

    Google Scholar 

  11. Okada M, Sumitomo H, Sumi A (1985) Carbohydr Res 143, 275

    Google Scholar 

  12. Hirasawa T, Okada M, Sumitomo H (1988) Macromolecules 21: 1566

    Google Scholar 

  13. Hirasawa T, Okada M, Sumitomo H (1988) Polym J 20: 587

    Google Scholar 

  14. Okada M, Hirasawa T, Sumitomo H (1989) Makromol. Chem. 190: 1289

    Google Scholar 

  15. Uryu T, Sakamoto Y, Hatanaka K, Matsuzaki K (1984) Macromolecules 17, 1307

    Google Scholar 

  16. Ponomarenko VA, Berman EL, Sakharov AM, Nysenko ZN (1984) In: Goethals EJ (ed) Cationic polymerization and related processes, Academic, London, p 155

    Google Scholar 

  17. Matyjaszewsky K (1983) Eur Polym J 19: 787

    Google Scholar 

  18. Okada M, Sumitomo H, Sumi A (1982) Macromolecules 15: 1238

    Google Scholar 

  19. Kobayashi K, Ichikawa H, Sumitomo H, Schuerch C (1988) Macromolecules 21: 542

    Google Scholar 

  20. Ichikawa H, Kobayashi K, Sumitomo H, Schuerch C (1988) Carbohydr Res 179: 315

    Google Scholar 

  21. Okada M, Sumitomo H, Komada H (1979) Macromolecules 12: 395

    Google Scholar 

  22. Okada M, Hirasawa T, Sumitomo H (1988) Makromol Chem Rapid Commun 9: 641

    Google Scholar 

  23. Okada M, Sumitomo H, Hirasawa T (1985) Macromolecules 18: 2345

    Google Scholar 

  24. Sumitomo H, Okada M (1987) In: Ottenbrite RM, Utracki LA, Inoue S (eds) Current topics in polymer science, Hanser, Munich, vol 1, p 15

    Google Scholar 

  25. Korshak VV, Golova OP, Sergeev VA, Merlis NA, Schneer RY (1961) Vysokomol Soedin 3: 477

    Google Scholar 

  26. Schuerch C (1981) Adv Carbohydr Chem Biochem 39: 157

    Google Scholar 

  27. Schuerch C (1985) Encyclopedia of polymer science and engineering, 2nd edn, John Wiley & Sons, New York, vol 13, p 162

    Google Scholar 

  28. Uryu T (1989) In: Penczek S (ed) Models of Biopolymers by Ring-Opening Polymerization, CRC Press, Boca Raton, FL, p 133

    Google Scholar 

  29. Micheel F, Broddle OE (1974) Liebig Ann Chem 702

    Google Scholar 

  30. Uryu T, Yamaguchi C, Morikawa K, Terui K, Kanai T, Matsuzaki K (1985) Macromolecules 18: 599

    Google Scholar 

  31. Yoshida T, Arai T, Mukai Y, Uryu T (1988) Carbohydr Res 177: 69

    Google Scholar 

  32. Uryu T, Yamanouchi J, Kato T, Higashi S, Matsuzaki K (1983) J Am Chem Soc 105: 6865

    Google Scholar 

  33. Hagino A, Yoshida S, Shinpuku T, Matsuzaki K, Uryu T (1986) Macromolecules 19: 1

    Google Scholar 

  34. Koyama Y, Harima K, Matsuzaki K, Uryu T (1985) J Polym Sci, Polym Chem Ed 23: 2989

    Google Scholar 

  35. Ichikawa H, Kobayashi K, Sumitomo H (1990) Macromolecules 23: 1884

    Google Scholar 

  36. Veruovic B, Schuerch C (1970) Carbohydr Res 14: 199

    Google Scholar 

  37. Masura U, Schuerch C (1970) Carbohydr Res 15: 65

    Google Scholar 

  38. Uryu T, Yamanaka M, Hemmi M, Hatanaka K (1986) Carbohydr Res 157: 157

    Google Scholar 

  39. Goethals EJ (1977) Adv Polym Sci 23: 103

    Google Scholar 

  40. Penczek S, Slomkowski S (1989) In: Eastmond GC, Ledwith A, Russo S, Sigwalt P (eds) Comprehensive polymer science. Pergamon, Oxford, vol 3, p 725

    Google Scholar 

  41. Ito K, Hashizuka Y, Yamashita Y (1977) Macromolecules 10: 821

    Google Scholar 

  42. Jacobson H, Stockmayer WH (1950) J Chem Phys 18: 1600

    Google Scholar 

  43. Okada M, Sumitomo H (1985) Makromol Chem, Suppl 14: 29

    Google Scholar 

  44. Okada M, Sumitomo H, Atsumi M (1984) Macromolecules 17: 1840

    Google Scholar 

  45. Okada M, Sumitomo M, Atsumi M (1983) Makromol Chem, Rapid Commun 4: 253

    Google Scholar 

  46. Tajima I, Okada M, Sumitomo H (1981) Macromolecules 14: 1180

    Google Scholar 

  47. Okada M, Tajima I, Sumitomo H (1984) In: Bailey WJ, Tsuruta T (eds) Contemporary topics in polymer science, Vol 4, Plenum, New York, p 415

    Google Scholar 

  48. Tanaka I, Tajima I, Hayakawa Y, Okada M, Bitoh M, Ashida T, Sumitomo H (1980) J Am Chem Soc 102: 7873

    Google Scholar 

  49. Imaeda M, Tanaka I, Ashida T, Tajima I, Okada M, Sumitomo H (1982) Polym J 14: 197

    Google Scholar 

  50. Sakuragi I, Tanaka I, Ashida T, Tajima I, Okada M, Sumitomo H (1982) 104: 6035

    Google Scholar 

  51. Tajima I, Okada M, Sumitomo H (1981) J Am Chem Soc 103: 4096

    Google Scholar 

  52. Okada M, Sumitomo H, Atsumi M (1984) J Am Chem Soc 106: 2101

    Google Scholar 

  53. Okada M, Sumitomo H, Ito K, Goto S, Atsumi M (1988) Polym J 20: 55

    Google Scholar 

  54. Okada M, Sumitomo H, Atsumi M, Hall HK Jr, Ortega RB (1986) Macromolecules 19: 503

    Google Scholar 

  55. Jones PG, Kirby AJ (1984) J Am Chem Soc 106: 6207

    Google Scholar 

  56. Okada M, Sumitomo H, Atsumi M, Hall HK Jr (1987) Macromolecules 20: 1199

    Google Scholar 

  57. Okada M, Sumitomo H, Yamada S, Atsumi M, Hall HK Jr, Chan RJH, Ortega RB (1986) Macromolecules 19: 953

    Google Scholar 

  58. Ceccarelli G, Andruzzi F, Paci M (1979) Polymer 20: 625

    Google Scholar 

  59. Burgi HB, Dunitz JD, Lehn JM, Wipff G (1974) Tetrahedron 30: 1563

    Google Scholar 

  60. Balackburn GM, Dodds HLH (1977) J Chem Soc, Perkin Trans 2 1977: 377

    Google Scholar 

  61. Andruzzi F, Pilcher G, Hacking JM, Cavell S (1980) Makromol Chem 181: 923

    Google Scholar 

  62. Boyesso B, Nakase Y, Sunner S (1966) Acta Chem Scand 20: 803

    Google Scholar 

  63. Hall HK Jr (1969) Macromolecules 2: 488

    Google Scholar 

  64. Hofman A, Szymanski R, Slomkowski S, Penczek S (1984) Makromol Chem 185: 655

    Google Scholar 

  65. Sumitomo H, Okada M (1978) Adv Polym Sci 28: 47

    Google Scholar 

  66. Sumitomo H, Hashimoto K (1985) Adv Polym Sci 64: 63

    Google Scholar 

  67. Hashimoto K, Sumitomo H, Yamamori H (1987) Polym J 19: 249

    Google Scholar 

  68. Hashimoto K, Sumitomo H, Yamamori H (1987) Polym J 19: 1139

    Google Scholar 

  69. Hashimoto K, Sumitomo H, Washio A (1988) Polym J 20: 615

    Google Scholar 

  70. Hashimoto K, Sumitomo H, Shinoda H, Washio A (1989) J Polym Sci Part C, Polym Lett 27: 307

    Google Scholar 

  71. Hashimoto K, Sumitomo H, Washio A (1989) J Polym Sci, Part A, Polym Chem 27: 1915

    Google Scholar 

  72. Hashimoto K, Sumitomo H (1984) J Polym Sci, Polym Chem Ed 22: 1733

    Google Scholar 

  73. Hashimoto K, Sumitomo H, Suzuki M (1987) Macromolecules 20: 2797

    Google Scholar 

  74. Moore JA, Pertain EM III (1982) J Polym Sci, Polym Lett 20: 521

    Google Scholar 

  75. Okada M, Sumitomo H, Mori H, Hall HK Jr, Chan RJH, Bruck M (1990) J Polym Sci, Part A, Polym Chem 28: 3251

    Google Scholar 

  76. Gu Y-X, Yamane T, Ashida T, Hashimoto K, Sumitomo H (1986) Bull Chem Soc Jpn 59: 2085

    Google Scholar 

  77. Okada M, Sumitomo H, Sassa T, Takai M, Hall HK Jr, Bruck M (1990) Macromolecules 23: 2427

    Google Scholar 

  78. Cho H, Choi K, Choi S (1985) J Polym Sci Polym Chem Ed 23: 623

    Google Scholar 

  79. Cho H, Choi S (1985) J Polym Sci Polym Chem. Ed 23: 1469

    Google Scholar 

  80. Hall HK Jr, De Blauwe F, Carr LJ, Rao VS (1976) J Polym Sci, Polym Symp 56: 101

    Google Scholar 

  81. Hall HK Jr, De Blauwe F (1974) J Am Chem Soc 96: 7265

    Google Scholar 

  82. Hall HK Jr, De Blauwe FG, Pyriadi T (1975) J Am Chem Soc 97: 3854

    Google Scholar 

  83. Burt RA, Chiang Y, Hall HK Jr, Kresge AJ (1982) J Am Chem Soc 104: 3687

    Google Scholar 

  84. Yokoyama Y, Padias AB, De Blauwe F, Hall HK, Jr (1980) Macromolecules 13: 252

    Google Scholar 

  85. Yokoyama Y, Padias AB, Bratoeff EA, Hall HK Jr (1982) Macromolecules 15: 11

    Google Scholar 

  86. Padias AB, Szymanski R, Hall HK, Jr (1985) In: McGrath JE (ed) Ring-opening polymerization kinetics, mechanisms and synthesis. ACS Symp Ser 286 p 313

    Google Scholar 

  87. Endo T, Saigo K, Bailey WJ (1980) J Polym Sci, Polym Lett Ed 18: 457

    Google Scholar 

  88. Hall HK Jr, Yokoyama Y (1980) Polym. Bull. 2: 281

    Google Scholar 

  89. Syzmanski R, Hall HK Jr (1983) J Polym Sci, Polym Lett. Ed 21: 177

    Google Scholar 

  90. Uno H, Endo T, Okawara M (1985) J Polym Sci, Polym Chem Ed 23: 63

    Google Scholar 

  91. Yokoyama Y, Hall HK Jr (1980) J Polym Sci Polym Chem Ed 18: 3133

    Google Scholar 

  92. Bailey WJ (1975) J Macromol Sci Chem A9: 849

    Google Scholar 

  93. Bailey WJ, Sun RL, Katsuki H, Endo T, Iwama H, Tsushima R, Saigo K, Bitritto MM (1977) In: Saegusa T, Goethals EJ (ed) Ring-opening polymerization, ACS Symp. Ser. 59: 38

    Google Scholar 

  94. Matyjaszewski K (1984) J Polym Sci, Polym Chem Ed 22: 29

    Google Scholar 

  95. Chikaoka S, Takata T, Endo T (1990) J Polym Sci, Part A, Polym Chem 28: 3101

    Google Scholar 

  96. Chikaoka S, Takata, Endo T (1990) Macromolecules 24: 331

    Google Scholar 

  97. Yokozawa T, Sato M, Endo T (1990) J Polym Sci, Part A, Polym Chem 28: 1841

    Google Scholar 

  98. Endo T, Okawara M, Yamazaki N, Bailey WJ (1981) J Polym Sci, Polym Chem Ed 19: 1283

    Google Scholar 

  99. Han YK, Choi SK (1983) J Polym Sci, Polym Chem Ed 21: 353

    Google Scholar 

  100. Pan C, Lu S, Bailey WJ (1987) Makromol Chem 188: 1651

    Google Scholar 

  101. Pan C, Wang Y (1986) Makromol Chem, Rapid Commun 7: 627

    Google Scholar 

  102. Sakai S, Fujinami T, Sakurai S (1973) J Polym Sci, Polym Lett Ed 11: 631

    Google Scholar 

  103. Takata T, Endo T (1988) Macromolecules 21: 900

    Google Scholar 

  104. Olah GA, Olah JA, Svoboda JJ (1973) Synthesis 490

    Google Scholar 

  105. Endo T, Sato H, Takata T (1988) Macromolecules 21: 1187

    Google Scholar 

  106. Takata T, Amachi K, Kitazawa K, Endo T (1989) Macromolecules 22: 3188

    Google Scholar 

  107. Takata T, Endo T (1988) Macromolecules 21: 2314

    Google Scholar 

  108. Hiraguri Y, Endo T (1987) J Am Chem Soc 109: 3779.

    Google Scholar 

  109. Gong MS, Chang S-I, Cho I (1989) Makromol Chem, Rapid Commun 10: 201

    Google Scholar 

  110. Sugiyama J, Yokozawa T, Endo T (1990) J Polym Sci, Part A, Polym Chem Ed 28: 3529

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1992 Springer-Verlag

About this chapter

Cite this chapter

Okada, M. (1992). Ring-opening polymerization of bicyclic and spiro compounds. Reactivities and polymerization mechanisms. In: Polymer Synthesis Oxidation Processes. Advances in Polymer Science, vol 102. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-55090-9_1

Download citation

  • DOI: https://doi.org/10.1007/3-540-55090-9_1

  • Received:

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-55090-7

  • Online ISBN: 978-3-540-46690-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics