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.
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Hall HK Jr (1958) J Am Chem Soc 80: 6412; (1960) J Am Chem Soc 82: 1209
Okada M (to be published) Prog Polym Sci
Sumitomo H, Okada M (1978) Adv Polym Sci 28: 47
Penczek S, Kubisa P, Matyjaszewski K (1980) Adv Polym Sci 37: 1
Yokoyama Y, Hall HK Jr (1982) Adv Polym Sci 42: 107
Sumitomo H, Okada M (1984) In: Ivin K, Saegusa T (eds) Ring-opening polymerization, Elsevier, London, vol I, p 229
Penczek S, Kubisa P, Matyjaszewski K (1985) Adv Polym Sci 68/69: 1
Hall HK Jr, Fr DeBlauwe, Carr LJ, Rao VS, Reddy GS (1976) J Polym Sci Symposia No 56: 101
Deslongchamps P (1975) Tetrahedron 31: 2463
Okada M, Sumitomo H, Sumi A, Sugimoto T (1984) Macromolecules 17: 2451
Okada M, Sumitomo H, Sumi A (1985) Carbohydr Res 143, 275
Hirasawa T, Okada M, Sumitomo H (1988) Macromolecules 21: 1566
Hirasawa T, Okada M, Sumitomo H (1988) Polym J 20: 587
Okada M, Hirasawa T, Sumitomo H (1989) Makromol. Chem. 190: 1289
Uryu T, Sakamoto Y, Hatanaka K, Matsuzaki K (1984) Macromolecules 17, 1307
Ponomarenko VA, Berman EL, Sakharov AM, Nysenko ZN (1984) In: Goethals EJ (ed) Cationic polymerization and related processes, Academic, London, p 155
Matyjaszewsky K (1983) Eur Polym J 19: 787
Okada M, Sumitomo H, Sumi A (1982) Macromolecules 15: 1238
Kobayashi K, Ichikawa H, Sumitomo H, Schuerch C (1988) Macromolecules 21: 542
Ichikawa H, Kobayashi K, Sumitomo H, Schuerch C (1988) Carbohydr Res 179: 315
Okada M, Sumitomo H, Komada H (1979) Macromolecules 12: 395
Okada M, Hirasawa T, Sumitomo H (1988) Makromol Chem Rapid Commun 9: 641
Okada M, Sumitomo H, Hirasawa T (1985) Macromolecules 18: 2345
Sumitomo H, Okada M (1987) In: Ottenbrite RM, Utracki LA, Inoue S (eds) Current topics in polymer science, Hanser, Munich, vol 1, p 15
Korshak VV, Golova OP, Sergeev VA, Merlis NA, Schneer RY (1961) Vysokomol Soedin 3: 477
Schuerch C (1981) Adv Carbohydr Chem Biochem 39: 157
Schuerch C (1985) Encyclopedia of polymer science and engineering, 2nd edn, John Wiley & Sons, New York, vol 13, p 162
Uryu T (1989) In: Penczek S (ed) Models of Biopolymers by Ring-Opening Polymerization, CRC Press, Boca Raton, FL, p 133
Micheel F, Broddle OE (1974) Liebig Ann Chem 702
Uryu T, Yamaguchi C, Morikawa K, Terui K, Kanai T, Matsuzaki K (1985) Macromolecules 18: 599
Yoshida T, Arai T, Mukai Y, Uryu T (1988) Carbohydr Res 177: 69
Uryu T, Yamanouchi J, Kato T, Higashi S, Matsuzaki K (1983) J Am Chem Soc 105: 6865
Hagino A, Yoshida S, Shinpuku T, Matsuzaki K, Uryu T (1986) Macromolecules 19: 1
Koyama Y, Harima K, Matsuzaki K, Uryu T (1985) J Polym Sci, Polym Chem Ed 23: 2989
Ichikawa H, Kobayashi K, Sumitomo H (1990) Macromolecules 23: 1884
Veruovic B, Schuerch C (1970) Carbohydr Res 14: 199
Masura U, Schuerch C (1970) Carbohydr Res 15: 65
Uryu T, Yamanaka M, Hemmi M, Hatanaka K (1986) Carbohydr Res 157: 157
Goethals EJ (1977) Adv Polym Sci 23: 103
Penczek S, Slomkowski S (1989) In: Eastmond GC, Ledwith A, Russo S, Sigwalt P (eds) Comprehensive polymer science. Pergamon, Oxford, vol 3, p 725
Ito K, Hashizuka Y, Yamashita Y (1977) Macromolecules 10: 821
Jacobson H, Stockmayer WH (1950) J Chem Phys 18: 1600
Okada M, Sumitomo H (1985) Makromol Chem, Suppl 14: 29
Okada M, Sumitomo H, Atsumi M (1984) Macromolecules 17: 1840
Okada M, Sumitomo M, Atsumi M (1983) Makromol Chem, Rapid Commun 4: 253
Tajima I, Okada M, Sumitomo H (1981) Macromolecules 14: 1180
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
Tanaka I, Tajima I, Hayakawa Y, Okada M, Bitoh M, Ashida T, Sumitomo H (1980) J Am Chem Soc 102: 7873
Imaeda M, Tanaka I, Ashida T, Tajima I, Okada M, Sumitomo H (1982) Polym J 14: 197
Sakuragi I, Tanaka I, Ashida T, Tajima I, Okada M, Sumitomo H (1982) 104: 6035
Tajima I, Okada M, Sumitomo H (1981) J Am Chem Soc 103: 4096
Okada M, Sumitomo H, Atsumi M (1984) J Am Chem Soc 106: 2101
Okada M, Sumitomo H, Ito K, Goto S, Atsumi M (1988) Polym J 20: 55
Okada M, Sumitomo H, Atsumi M, Hall HK Jr, Ortega RB (1986) Macromolecules 19: 503
Jones PG, Kirby AJ (1984) J Am Chem Soc 106: 6207
Okada M, Sumitomo H, Atsumi M, Hall HK Jr (1987) Macromolecules 20: 1199
Okada M, Sumitomo H, Yamada S, Atsumi M, Hall HK Jr, Chan RJH, Ortega RB (1986) Macromolecules 19: 953
Ceccarelli G, Andruzzi F, Paci M (1979) Polymer 20: 625
Burgi HB, Dunitz JD, Lehn JM, Wipff G (1974) Tetrahedron 30: 1563
Balackburn GM, Dodds HLH (1977) J Chem Soc, Perkin Trans 2 1977: 377
Andruzzi F, Pilcher G, Hacking JM, Cavell S (1980) Makromol Chem 181: 923
Boyesso B, Nakase Y, Sunner S (1966) Acta Chem Scand 20: 803
Hall HK Jr (1969) Macromolecules 2: 488
Hofman A, Szymanski R, Slomkowski S, Penczek S (1984) Makromol Chem 185: 655
Sumitomo H, Okada M (1978) Adv Polym Sci 28: 47
Sumitomo H, Hashimoto K (1985) Adv Polym Sci 64: 63
Hashimoto K, Sumitomo H, Yamamori H (1987) Polym J 19: 249
Hashimoto K, Sumitomo H, Yamamori H (1987) Polym J 19: 1139
Hashimoto K, Sumitomo H, Washio A (1988) Polym J 20: 615
Hashimoto K, Sumitomo H, Shinoda H, Washio A (1989) J Polym Sci Part C, Polym Lett 27: 307
Hashimoto K, Sumitomo H, Washio A (1989) J Polym Sci, Part A, Polym Chem 27: 1915
Hashimoto K, Sumitomo H (1984) J Polym Sci, Polym Chem Ed 22: 1733
Hashimoto K, Sumitomo H, Suzuki M (1987) Macromolecules 20: 2797
Moore JA, Pertain EM III (1982) J Polym Sci, Polym Lett 20: 521
Okada M, Sumitomo H, Mori H, Hall HK Jr, Chan RJH, Bruck M (1990) J Polym Sci, Part A, Polym Chem 28: 3251
Gu Y-X, Yamane T, Ashida T, Hashimoto K, Sumitomo H (1986) Bull Chem Soc Jpn 59: 2085
Okada M, Sumitomo H, Sassa T, Takai M, Hall HK Jr, Bruck M (1990) Macromolecules 23: 2427
Cho H, Choi K, Choi S (1985) J Polym Sci Polym Chem Ed 23: 623
Cho H, Choi S (1985) J Polym Sci Polym Chem. Ed 23: 1469
Hall HK Jr, De Blauwe F, Carr LJ, Rao VS (1976) J Polym Sci, Polym Symp 56: 101
Hall HK Jr, De Blauwe F (1974) J Am Chem Soc 96: 7265
Hall HK Jr, De Blauwe FG, Pyriadi T (1975) J Am Chem Soc 97: 3854
Burt RA, Chiang Y, Hall HK Jr, Kresge AJ (1982) J Am Chem Soc 104: 3687
Yokoyama Y, Padias AB, De Blauwe F, Hall HK, Jr (1980) Macromolecules 13: 252
Yokoyama Y, Padias AB, Bratoeff EA, Hall HK Jr (1982) Macromolecules 15: 11
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
Endo T, Saigo K, Bailey WJ (1980) J Polym Sci, Polym Lett Ed 18: 457
Hall HK Jr, Yokoyama Y (1980) Polym. Bull. 2: 281
Syzmanski R, Hall HK Jr (1983) J Polym Sci, Polym Lett. Ed 21: 177
Uno H, Endo T, Okawara M (1985) J Polym Sci, Polym Chem Ed 23: 63
Yokoyama Y, Hall HK Jr (1980) J Polym Sci Polym Chem Ed 18: 3133
Bailey WJ (1975) J Macromol Sci Chem A9: 849
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
Matyjaszewski K (1984) J Polym Sci, Polym Chem Ed 22: 29
Chikaoka S, Takata T, Endo T (1990) J Polym Sci, Part A, Polym Chem 28: 3101
Chikaoka S, Takata, Endo T (1990) Macromolecules 24: 331
Yokozawa T, Sato M, Endo T (1990) J Polym Sci, Part A, Polym Chem 28: 1841
Endo T, Okawara M, Yamazaki N, Bailey WJ (1981) J Polym Sci, Polym Chem Ed 19: 1283
Han YK, Choi SK (1983) J Polym Sci, Polym Chem Ed 21: 353
Pan C, Lu S, Bailey WJ (1987) Makromol Chem 188: 1651
Pan C, Wang Y (1986) Makromol Chem, Rapid Commun 7: 627
Sakai S, Fujinami T, Sakurai S (1973) J Polym Sci, Polym Lett Ed 11: 631
Takata T, Endo T (1988) Macromolecules 21: 900
Olah GA, Olah JA, Svoboda JJ (1973) Synthesis 490
Endo T, Sato H, Takata T (1988) Macromolecules 21: 1187
Takata T, Amachi K, Kitazawa K, Endo T (1989) Macromolecules 22: 3188
Takata T, Endo T (1988) Macromolecules 21: 2314
Hiraguri Y, Endo T (1987) J Am Chem Soc 109: 3779.
Gong MS, Chang S-I, Cho I (1989) Makromol Chem, Rapid Commun 10: 201
Sugiyama J, Yokozawa T, Endo T (1990) J Polym Sci, Part A, Polym Chem Ed 28: 3529
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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
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