Ring-opening polymerization of heterocycles bearing substituted and unsubstituted exo-methylene groups - A review

Acta Polymerica

Volumn 50, Issue 1, 1999, Pages 1-19

  Kleinm, E ^a   Schulze, T ^b  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b Thüringisches Institut Fürtextil Und Kunststoff Forschung E v   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL RESINS; FREE RADICAL POLYMERIZATION; ISOMERIZATION; MOLECULAR STRUCTURE; MONOMERS; POLYACRYLATES; POLYCARBONATES; RING OPENING POLYMERIZATION;

CYCLIC KETENE ACETALS; ENOLETHERS; LACTAMES; LACTONES;

AROMATIC POLYMERS;

EID: 0032785829     PISSN: 03237648     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-4044(19990101)50:1<1::aid-apol1>3.0.co;2-o     Document Type: Article

References (138)

1. W.J. Bailey, T. Endo, B. Gapud, Y.-N. Lin, Z. Ni, C.-Y. Pan, S.E. Shaffer, S.-R. Wu, N. Yamazaki, K. Yonezawa, J. Macromol. Sci.,Chem. 1984, A21, 979.
2. W.J. Bailey, P.Y. Chen, S.-C. Chen, W.-B. Chiao, T. Endo, B. Gapud, Y.-N. Lin, Z. Ni, C.-Y. Pan, S.E. Shaffer, L. Sidney, S.-R. Wu, N. Yamamoto, N. Yamazaki, K. Yonezawa, J. Macromol. Sci., Client. 1984, A21, 1611.
3. W.J. Bailey, Makwmol. Chem., Suppl. 1985,13, 171.
4. W.J. Bailey, Polym. J. 1985,17, 85.
5. W.J. Bailey, J.L. Chou, P.-Z. Feng, B. Issari, V. Kuruganti, L.-L. Zhou, J. Macromol. Sci., Chem. 1988, A25, 781.
6. W.J. Bailey, J.L. Chou, P.-Z. Feng, V. Kuruganti, Acta Polym. 1988,39, 335.
7. W.J. Bailey, J.-M. Gu, Y.-N. Lin, Z.-F. Zheng, L.-L. Zhou, Makromol. Chem., Macromol. Symp. 1991,42/43, 195.
8. W.J. Bailey, P.-Y. Pan, S.-C. Chen, Makromol. Chem., Makwmol. Symp. 1986,6,81.
9. W.J. Bailey, A. Arfaei, P.-Y. Chen, Proceedings IUPAC 28th Macromoleciilar Symp., Amherst, MA, July 12-16, 1982, p. 214.
10. T. Endo, F. Sanda, Polymeric Materials Encyclopedia, 10, 7549-7576.
11. Expanding Monomers (Eds: R.K. Sadir, R.M. Luck), CRC Press, Boca Raton, McGrath FL, 1992.
12. W.J. Bailey, in Ring-opening polymerization (Ed: J.E. McGrath), ACS Symp. Series 286, Am. Chem. Soc., Washington D.C., 1985, p. 47.
13. T. Endo, T. Yokozawa, New Methods Polym. Synth. Part C 1992, 155.
14. T. Endo, T. Takata, T. Yokozawa, N. Kihara, T. Koizumi, I. Tomita, New. Fund. Mater. Part C1993, 321.
15. D. Colombani, Prog. Polym. Sci. 1996,465.
16. R.F. Brady, Jr., J. Macromol. Sci., Rev. Macromol. Chem. Phys. 1992, C32, 135.
17. W.J. Bailey, L.N. Sidney, S.E. Shaffer, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem. 1984,20, 643.
18. P. Hudrlik, A. Hudrlik, C. Wan, J. Org. Chem. 1975,40, 1116.
19. L.N. Sidney, S.E. Shaffer, W.J. Bailey, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem. 1981, 22, 373.
20. M. Ueda, H. Mori, H. Ito, J. Polym. Sci., Polym. Chem. 1990, 28, 2597.
21. T. Schulze, J. Letsch, E. Klemm, J. Polym. Sci., Polym. Chem. 1996,34, 81.
22. W.J. Bailey, Z. Ni, S.-R. Wu, J. Polym. Sci., Polym. Chem. 1982, 20,3021.
23. W.J. Bailey, B. Gapud, Y.-N. Lin, Z. Ni, S.-R. Wu, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem. 1984,27(1), 142.
24. W.J. Bailey, A. Arfaei, RY. Chen, S.-C. Chen, T. Endo, C.-Y. Pan, Z. Ni, S. Shatter, L. Sidney, S.-R. Wu, N. Yamazaki, Pro-ceedings IUPAC 28th Macromoleciilar Symp., Amherst, Massachussetts, July 12-16,1982, p. 214.
25. J. Letsch, E. Klemm, J. Polym. Sci., Polym. Cliem. 1994, 32, 2867.
26. S. Femandez-Reina, J. Letsch, E. Klemm, Acta Polym. 1996, 47, 204.
27. I. Cho, N.-S. Gong, Pollimo 1985, 9, 503, CA 1986, 104, 149 469.
28. W.J. Bailey, Polym. Prepr., Am. Chem. Soc., Dlv. Polym. Chem. 1984,25(7;, 210.
29. T. Itoh, I. Katoh, T. Satoh, S. Iwatsuki, J. Polym. Sci., Polym. Chem. 1995,33, 1537.
30. M.K. Akkapeddi, Macromoleciiles 1979,12,546.
31. M. Ueda, M. Takahashi, Y. Imai, C.U. Pittman, Jr. J. Polym. Sci., Polym. Chem. 1982,20, 2819.
32. J. Suenaga, D.M. Sutherlin, J.K. Stille, Macromoleciiles 1984, 77,2913.
33. H. Ito, M. Ueda, Macromokailes 1990,23, 2885.
34. V. Percée, J.H. Wang, Makromol. Chem., Macromol. Symp. 1992, 54/55,561.
35. H. Fukuda, M. Hirota, Y. Nakashima, J. Polym. Sci., Polym. Lett. Ed. 1983,2], 177.
36. W.J. Bailey, S.-R. Wu, Z.Ni, J. Macromol. Sci., Chem. 1982, A18, 973.
37. P.C. Zhu, C.U. Pittman, Jr., J. Polym. Sci., Polym. Chem. 1996, 34, 73.
38. P.C. Zhou, Y. Liu, J. Lin, C.U. Pittman, Jr., J. Polym. Sci., Polym. Chem. 1996, 34, 2195.
39. E. Diaz-Barra, A. de la Hoz, A. Diaz-Ortiz, P. Prieto, Synlett 1992, 893.
40. T. Schulze, E. Klemm, Makromol. Chem. 1993,194,2087.
41. T. Schulze, Ph. D. thesis, University of Jena, 1994.
42. H. Fukuda, M. Hirota, T. Endo, Tetrahedron Lett. 1986,27, 1587.
43. W.J. Bailey, S.-R. Wu, Makromol. Chem. 1982,183, 1913.
44. T. Endo, N. Yako, K. Azuma, K. Nate, Makromol. Chem. 1985, 186, 1543.
45. I. Cho, M.S. Gong, J. Polym. Sei, Polym. Lett. Ed. 1982,20,361.
46. M. Acar, Y. Manbu, K. Yamamoto, T. Endo, J. Polym. Sci., Polym. Chem. 1989,27,4441.
47. T. Yokozawa, J. Takagi, T. Endo, J. Polym. Sci., Polym. Chem. 1989,27,291.
48. T. Yokozawa, K. D. Ando, T. Endo, Macromoleciiles 1994, 27, 1978.
49. I. Cho, B.-J. Lee, J. Polym. Sci., Polym. Lett. 1984,22,487.
50. T. Yokozawa, J. Tagaki, T. Endo, Makromol. Chem., Rapid.Commun. 1991,12, 553.
51. J.V. Crivello, R. Malik, Y.-L. Lai, J. Polin. Sci., Polym. Chem. 1996,34,3091.
52. J.V. Crivello, Y.-L. Lai, R. Malik, J. Polin. Sci., Polym. Chem. 1996,34,3103.
53. T. Mukaiyama, T. Fujisawa, H. Nohira, T. Hywsaja, J. Org. Chem. 1962, 27,3337.
54. W.J. Bailey, L.-L. Zhou, Tetrahedron Lett. 1991,32, 1539.
55. I. Cho, S.-K. Kirn, J. Polym. Sci., Polym. Lett. 1990,28,417.
56. H. Fukuda, M. Oda, T. Endo, Makromol. Chem., Rapid Commun. 1994, 75,579.
57. H. Fukuda, M. Oda, T. Endo, Macromoleciiles 1995,28,4319.
58. H. Orth, Angew. Chem. 1952, 64,544.
59. M. Goodman, A. Abe, J. Polym. Sci. 1964, A2, 3471.
60. M.K. Akkapeddi, H.K. Reimschüssel, Macromoleciiles 1979, 12, 827.
61. E. Taskmen, J. Org. Chem. 1978,43, 2772.
62. C.-Y. Pan, Z. Wu, W.J. Bailey, J. Polym. Sci. Polym. Lett. 1987, 25,243.
63. B. Reed, J. Stansbury, P. Antonucci, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem. 1992,33(2), 520.
64. I. Cho, B.-G. Kirn, Y.-C. Park, C.-B. Kim, M.-S. Gong, Makromol. Chem., Rapid Commun. 1991,12, 141.
65. C.-Y. Pan, Z. Wu, Q.-R. Zhu, W.J. Bailey, J. Macromol. Sci. 1987, A25, 27.
66. H. Fukuda, M. Hirota, Y. Nakashima, J. Polym. Sci., Polym. Chem. 1982,20, 1401.
67. C. Bolln, H. Frey, R. Miilhaupt, J. Polym. Sci., Polym. Chem. 1995,33,587.
68. S. Maraviu, B.C. Simionescu, Eur. Polym. J. 1994,30, 1339.
69. S. Morario, E.C. Buruiano, B.C. Simionescu, Polym. Bull. 1993,30,1.
70. S.-J. Lee, J.-K. Park, M.-S. Gong, Bull. Korean. Chem. Soc. 1995,16,769.
71. M.-S. Gong, T.-M. Kim, J.K. Park, Polymer (Korea) 1994, 18, 651.
72. T.-M. Kim, Y. Kim, M.-S. Gong, Macromol. Rapid Commun. 1994, 75, 639.
73. Y. Hiraguri, T. Endo, J. Polym. Sci., Polym. Chem. 1989, 27, 4403.
74. K. Konno, J. Sigiyama, M. Ueda, T. Endo, Polym. Prepr. Jpn. 1992,47,195.
75. M.-S. Gong, S.-I. Chang, I. Cho, Makromol. Chem., Rapid Commun. 1989,10,201.
76. Y. Hiraguri, T. Endo, J. Am. Chem. Soc. 1987, 709, 3779.
77. Y. Hiraguri, T. Endo, J. Polym. Sci., Polym. Lett. 1989, 27, 1.
78. Y. Hiraguri, T. Endo, J. Polym. Sci., Polym. Chem. 1989, 27, 2135.
79. T. Koizumi, Y. Hasegawa, T. Takata, T. Endo, J. Polym. Sci., Polym. Chem. 1994, 32, 3193.
80. Y. Hiraguri, T. Sugizaki, T. Endo, Macromolecules 1990,23, 1.
81. Y. Hiraguri, T. Endo, J. Polym. Sci., Polym. Chem. 1990, 28, 2881.
82. Y. Hiraguri, T. Endo, J. Polym. Sci., Polym. Chem. 1992, 30, 689.
83. J.-I. Sugiyama, T. Yokozawa, T. Endo, J. Polym. Sci., Polym. Chem. 1993,31,2173.
84. J.-I. Sugiyama, T. Yokozawa, T. Endo, Macromolecules 1993, 26,2842.
85. J.-I. Sugiyama, T. Yokozawa, T. Endo, Macromolecules 1994, 27, 1987
86. J.-I. Sugiyama, T. Yokozawa, T. Endo, J. Am. Chem. Soc. 1994, 775,2041.
87. J.-I. Sugiyama, T. Yokozawa, T. Endo, Macromolecules 1994, 27,5536.
88. J.-I. Sugiyama, S.-I. Omokawa, M. Ueda, T. Endo, Makromol. Chem., Rapid Commun. 1993,14, 643.
89. J.-I. Sugiyama, K. Tanikawa, T. Okada, K. Noguchi, M. Ueda, T. Endo, Tetrahedron Lett. 1994,35, 3111.
90. J.-I. Sugiyama, M. Ueda, T. Endo, Macromolecules 1995, 28, 6735.
91. J. Park, T. Yokozawa, T. Endo, Makromol. Chem. 1993, 194, 2017.
92. J. Park, N. Kihara, T. Ikeda, T. Endo, J. Polym. Sci., Polym. Chem. 1993,57, 1083.
93. J. Park, T. Yokozawa, T. Endo, J. Polym. Sci., Polym. Chem. 1993,37,1141.
94. J. Park, N. Kihara, T. Endo, Macromol. Chem. Phys. 1996, 797, 2455.
95. J. Park, N. Kihara, M. Kobayashi, T. Endo, J. Polym. Sci., Polym. Chem. 1994,32, 199.
96. J. Park, W. Choi, N. Kihara, T. Endo, J. Polym. Sci., Polym. Chem. 1994,32, 983.
97. [97J K. Tanikawa, J. Sigiyama, M. Ueda, T. Endo, Polym. Prepr. Jpn. 1992,41, 194.
98. T. Yokozawa, R. Hayashi, T. Endo, Macromolecules 1992, 25, 3313.
99. T. Yokozawa, R. Hayashi, T. Endo, J. Polym. Sci., Polym. Chem. 1990,28, 3739.
100. J.E. Heller, A.S. Dreiding, B.R. O'Conner, H.E. Simmons, G.L. Buchanon, R.A. Raphael, R. Taylor, Helv. Chiin. Ada 1973,56, 272.
101. W.J. Bailey, P.-Z. Feng, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem. 1987, 25(7;, 154.
102. F. Zeuner, N. Moszner, V. Rheinberger, J. prakt. Chem. 1995, 337,478.
103. V.R. Likhterev, V.S. Ellis, L.A. Temovskii, Klüm. Geterosikl. Socdin. 1985, (10), 1316, CA 1986,104, 186 333.
104. M. van Beylen, C. Samyn, Makromol. Chem. 1990,191,2485.
105. M. Ueda, M. Honda, J.-I. Sugiyama, H. Ito, J. Polym. Sci., Polym. Chem. 1993,31, 949.
106. M. Ueda, M. Takahashi, T. Suzuki, Y. Imai, C.U. Pittman, Jr., J. Polym. Sci., Polym. Phys. 1983,20, 1139.
107. C. Samyn, G. Smets, Makromol. Chem. 1983, 184,949.
108. G.M. Iskander, T.R. Ovenell, T.P. Davis, Macromol. Chem. Phys. 1996, 797,3123.
109. I. Cho, T.-W. Lee, Makromol Chem., Rapid Commun. 1989, 10,453.
110. S. Kobayashi, J. Kadokawa, Y. Matsumura, I.F. Yen, H. Uyama, Macromol. Reports 1992, A29 (Suppl. 3), 243.
111. S. Kobayashi, J. Kadokama, S. Shoda, H. Oyama, Macromol. Reports 1991, A 28, 1.
112. I. Koichi, T. Yokozawa, T. Endo, Polym. Prepr. Jpn. 1991, 40, 167(Engl.Ed. E 37).
113. Z. Ni, W.J. Bailey, Gaofenzi Xuebao 1987, (5), 379-83, CA 1988,705,132401.
114. P.C. Zhou, C.U. Pittman, Jr., J. Polym. Sci., Polym. Chem. 1996,34,169.
115. T. Schulze, E. Klemm, Augen: Makromol. Chem. 1995, 229, 123.
116. T. Schulze, E. Klemm, Polym. Bull. 1993,31,409.
117. J. Heller, D.W.H. Pende, R.F. Heiwink, J. Polym. Sci., Polym. Lett. 1980,18, 619.
118. W.J. Bailey, P.-J. Zeng, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1995,36(2), 241.
119. M. Ueda, H. Toyota, A. Sone, H. Ito, J. Polym. Sci., Polym. Chem. 1993, 31, 1895.
120. M. Ueda, M. Takahashi, Y. Imai, C.U. Pittman, Jr., Macromolecules 1983, 76, 1300.
121. R.A. Evans, G. Moad, E. Rizzardo, S.H. Thang, Macromolecnles 1994,27,7935.
122. T. Endo, M. Okawara, W.J. Bailey, K. Azuma, K. Nate, H. Yokono, J. Polym. Sei,. Polym. Lett. 1983,27, 373.
123. S. Jim, K.E. Gonzalves, Macromoleciiles 1997,30, 3104.
124. Y. Wie, E.J. Connors, X. Jia, B. Wang, C. Deng, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1995,36(2), 241.
125. P.C. Zhou, Z. Wu, C.U. Pittman, Jr., J. Polym. Sci., Polym. Chem. 1997,35,485.
126. [ 126] W.J. Bailey, Z. Ni, S.-R. Wu, Macromoleciiles 1982, 75,711.
127. B. Reed, J. Stansbury, J. Antonucci, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem. 1992,33(2), 507.
128. T. Schulze, E. Klemm, Macromol. Chem. Phys. 1995, 796,567.
129. T. Schulze, E. Klemm, Angew. Makromol. Chem. 1998, 255, 67.
130. N. Moszner, T. Völkel, N. Rheinberger, Macromol. Chem. Phys. 1997, 79S, 749.
131. S. Fernandez-Reina, E. Klemm, Macromol. Chem. Phys. 1998, 799, 563.
132. Y. Hiraguri, Y. Tokiwa, J. Polym. Sci., Polym. Chem. 1993, 31, 3159.
133. Methoden der Organischen Chemie (Houben-Weyl), O/O- und O/S-Acetale, (Eds: 77. Hagemann, D. Klamann), E 14a/Teil 1, G. Thieme-Verlag, Stuttgart, New York 1991.
134. S.M. McElvian, W.D. Davie, J. Am. Chem. Soc. 1951, 73, 1400.
135. S.M. McElvian, M.J. Curry, J. Am. Chem. Soc. 1948, 70, 3781.
136. W.J. Bailey, L.-L. Zhou, Tetrahedron Lett. 1991,32, 1539.
137. E. Diaz-Barra, A. de la Hoz, P. Prieto, Synth. Commun. 1993, 23, 1935.
138. V. Haack, R. Kohl, E. Klemm, Polym. Bull. 1997,39 271.