Advertisement

Ring-opening polymerization of atom-bridged and bond-bridged bicyclic ethers, acetals and orthoesters

  • Y. Yokoyama
  • H. K. HallJr.
Conference paper
Part of the Advances in Polymer Science book series (POLYMER, volume 42)

Abstract

During these two decades, the polymerization of bicyclic compounds has been studied to obtain basic knowledge on ring-opening polymerization and for industrial and biomedical applications. In 1961, Korshak et al.1) reported the stereospecific polymerization of 1,6-anhydro-2,3,4-tri-O-methyl-D-glucopyranose. Schuerch and coworkers2–3) have developed the chemical synthesis of polysaccharides of biomedical interest. Very recently, Sumitomo and Okada4) reviewed the reaction mechanism of the ring-opening polymerization and the structures and properties of the resulting polymers of bicyclic acetals, bicyclic oxalactones, bicyclic oxalactams, and related heterobicyclo compounds. Tadokoro5, 6) reported the structure of crystalline polymers by X-ray diffraction, infrared, Raman spectroscopy, and energy calculations. Many workers7) have studied the structure of oxygen-containing polymers in solution. Finally, the anomeric effect and gauche effect have been made clear by many workers8, 9).

Therefore, we hope to discuss the polymerization mechanism and polymerizability of bicyclic compounds containing oxygen atoms and their relation to the monomer and polymer structures. Finally, some biomedical application of polymers will be mentioned.

The review will be limited to atom- and bond-bridged bicyclic monomers. The important work of Bailey on the polymerization of spiro bicyclo orthoesters and spiro bicyclic orthocarbonates has been adequately described elsewhere10a–d, 60–63). The outstanding and systematic body of work by Schuerch2, 3) and others on the ring opening polymerization of bicyclic acetals derived from carbohydrate precursors will also not be covered here.

Keywords

Anomeric Effect Cyclohexane Ring Polymerization Mechanism Ring Strain Bicyclic Compound 
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.

8 References

  1. 1.
    Korshak, V. V. et al.: Vysokomol. Soedin. 3, 477 (1961); CA 56, 5830 (1962)Google Scholar
  2. 2. (a)
    Schuerch, C.: Adv. Polym. Sci. 10, 173 (1972)Google Scholar
  3. 2. (b)
    Schuerch, C.: Acc. Chem. Res. 6, 184 (1973)Google Scholar
  4. 2. (c)
    Schuerch, C.: Encycl. Polym. Sci. and Technol. Suppl., Vol. 1, 510 (1976)Google Scholar
  5. 3.
    Kobayoshi, S., Eby, R., Schuerch, C.: Biopolymers 16, 415 (1977)PubMedGoogle Scholar
  6. 4.
    Sumitomo, H., Okada, M.: Adv. Polym. Sci. 28, 47 (1978)Google Scholar
  7. 5.
    Tadokoro, H.: Macromol. Rev. 1, 119 (1967)Google Scholar
  8. 6.
    Tadokoro, H.: Structure of Crystalline Polymers, Wiley-Interscience, New York, 1979Google Scholar
  9. 7.
    Mark, J. E.: Acc. Chem. Res. 12, 49 (1979)Google Scholar
  10. 8.
    Eliel, E. L. et al.: Conformation Analysis, Wiley-Interscience, New York, N. Y., 1965Google Scholar
  11. 9.
    Szarek, W. A., Horton, D., (Ed.): Anomeric Effect, Origin and Consequences, ACS Symp. Series 87, Amer. Chem. Soc., Washington, D. C., 1979Google Scholar
  12. 10. (a)
    Bailey, W. J.: J. Macromol. Sci. Chem. A 9, 849 (1975)Google Scholar
  13. 10. (b)
    Bailey, W. J., Iwama, H., Tsushima, R.: J. Polym. Sci., Symp. 56, 117 (1976)Google Scholar
  14. 10. (c)
    Endo, T., Bailey, W. J.: Makromol. Chem. 176, 2897 (1975)Google Scholar
  15. 10. (d)
    Endo, T., Katsuki, H., Bailey, W. J.: ibid. 177, 3231 (1970)Google Scholar
  16. 11.
    Wilkins, J. P.: U.S. Pat. 2, 764, 559 (1956); CA 51, 4053g (1957)Google Scholar
  17. 12.
    Campbell, T. W.: U.S. Pat. 2, 831, 825 (1958); CA 52, 13316i (1958)Google Scholar
  18. 13.
    Wittbecker, E. L., Hall, H. K. Jr., Campbell, T. W.: J. Amer. Chem. Soc. 82, 1218 (1960)Google Scholar
  19. 14.
    Giusti, P., Andruzzi, F.: Ann. Chem. (Rome) 56, 973 (1966)Google Scholar
  20. 15.
    Magagnini, P. L. et al.: Ann. Chem. (Rome) 57, 1493 (1967)Google Scholar
  21. 16.
    Baccaredda, M. et al.: Chim. Ind. (Milano) 50, 81 (1968)Google Scholar
  22. 17.
    Giusti, P., Andruzzi, F., di Maina, M.: Chin. Ind. (Milano) 50, 121 (1968)Google Scholar
  23. 18.
    Giusti, P. et al.: Makromol. Chem. 128, 1 (1969)Google Scholar
  24. 19.
    Baccaredda, M. et al.: J. Polymer Sci. Part C 31, 157 (1979)Google Scholar
  25. 20.
    Saegusa, T. et al.: Macromolecules 5, 233 (1972)Google Scholar
  26. 21.
    Saegusa, T. et al.: ibid. 5, 236 (1972)Google Scholar
  27. 22.
    Saegusa, T. et al.: ibid. 5, 815 (1972)Google Scholar
  28. 23.
    Andruzzi, F., Barnes, D. S., Plesch, P. H.: Makromol. Chem. 176, 2053 (1975)Google Scholar
  29. 24.
    Saegusa, T., Motoi, M., Suda, H.: Macromolecules 9, 231 (1976)Google Scholar
  30. 25.
    Saegusa, T., Motoi, M., Suda, H.: ibid. 9, 526 (1976)Google Scholar
  31. 26.
    Andruzzi, F. et al.: Makromol. Chem. 178, 2367 (1977)Google Scholar
  32. 27.
    Kops, J., Spanggaard, H.: Makromol. Chem. 151, 21 (1972)Google Scholar
  33. 28.
    Saegusa, T. et al.: Polym. J. 11, 113 (1979)Google Scholar
  34. 29.
    Saegusa, T., Hodaka, T., Fujii, H.: Polym. J. 2, 670 (1971)Google Scholar
  35. 30.
    Hvilsted, S., Kops, J.: Macromolecules 12, 889 (1979)Google Scholar
  36. 31.
    Kops, J., Larsen, E., Spanggaard, H.: J. Polym. Sci., Polym. Symp. 56, 91 (1976)Google Scholar
  37. 32.
    Kops, J., Spanggaard, H.: Makromol. Chem. 175, 3077 (1974)Google Scholar
  38. 33.
    Crivello, J. V., Lam, J. H. W.: J. Polym. Sci., Polym. Symp. 56, 383 (1976)Google Scholar
  39. 34.
    Chang, E. Y. C.: Ph. D. Dissertation, Univers. Pennsylvania, 1961Google Scholar
  40. 35.
    Ceccarelli, G., Andruzzi, F.: Makromol. Chem. 180, 1371 (1979)Google Scholar
  41. 36.
    Irie, M., Yamamoto, Y., Hayashi, K.: Pure Appl. Chem. 49, 455 (1977)Google Scholar
  42. 37.
    Crivello, J. V., Lam, J. H. W., Volantee, C. N.: J. Radiat. Curing 4, 2 (1977)Google Scholar
  43. 38.
    Malhotra, S. L., Blanchard, L. P.: J. Macromol. Sci. Chem. A 13, 1379 (1978)Google Scholar
  44. 39.
    Irie, M. et al.: J. Polym. Sci., Polym. Chem., 17, 815 (1979)Google Scholar
  45. 40.
    Hall, H. K. Jr. et al.: J. Polym. Sci., Polym. Symp. 56, 101 (1976)Google Scholar
  46. 41.
    Okada, M., Sumitomo, H., Irii, S.: Makromol. Chem. 177, 2331 (1976)Google Scholar
  47. 42.
    Tamura, A. et al.: Kogyo Kagaku Zasshi (J. Chem. Soc. Jpn., Ind. Chem. Sect.) 68, 2271 (1965)Google Scholar
  48. 43.
    Kops, J.: J. Polym. Sci. Part A 1, 10, 1275 (1972)Google Scholar
  49. 44.
    Sumitomo, H., Okada, M., Hibino, Y.: J. Poly. Sci., Polym. Lett. Ed. 10, 871 (1972)Google Scholar
  50. 45.
    Hall, H. K. Jr., Steuck, M. J.: J. Polym. Sci., Polym. Chem. Ed. 11, 103 (1973)Google Scholar
  51. 46.
    Okada, M., Sumitomo, H., Hibino, Y.: Polym. J. 6, 256 (1974)Google Scholar
  52. 47.
    Okada, M., Sumitomo, H., Hibino, Y.: ibid. 7, 511 (1975)Google Scholar
  53. 48.
    Komada, H., Okada, M., Sumitomo, H.: Macromolecules 12, 5 (1979)Google Scholar
  54. 49.
    Okada, M., Sumitomo, H., Komada, H.: ibid. 12, 395 (1979)Google Scholar
  55. 50.
    Okada, M., Sumitomo, H., Komada, H.: ibid. 178, 343 (1977)Google Scholar
  56. 51.
    Okada, M., Sumitomo, H., Komada, H.: ibid. 179, 949 (1978)Google Scholar
  57. 52.
    Komada, H., Okada, M., Sumitomo, H.: ibid. 179, 2859 (1978)Google Scholar
  58. 53.
    Okada, M. et al.: ibid. 180, 813 (1979)Google Scholar
  59. 54.
    Hall, H. K. Jr. et al.: J. Amer. Chem. Soc. 96, 7265 (1974)Google Scholar
  60. 55.
    Kops, J., Spanggaard, H.: Makromol. Chem. 176, 299 (1975)Google Scholar
  61. 56.
    Yokoyama, Y. et al.: Macromolecules 13, 252 (1980)Google Scholar
  62. 57.
    Hall, H. K. Jr., Yokoyama, Y.: Polym. Bull. 2, 281 (1980)Google Scholar
  63. 58.
    Yokoyama, Y., Hall, H. K. Jr.: J. Polym. Sci., Polym. Chem. Ed. 18, 3133 (1980)Google Scholar
  64. 59.
    Yokoyama, Y. et al.: Macromolecules, submittedGoogle Scholar
  65. 60.
    Bailey, W. J. et al.: ACS Symp. Series 59, 38 (1977)Google Scholar
  66. 61.
    Bailey, W. J., Saigo, K.: Abstr. ACS Meet. Houston, March, 1980, p. 4Google Scholar
  67. 62.
    Endo, T., Saigo, K., Bailey, W. J.: J. Polym. Sci., Polym. Lett. 18, 457 (1980)Google Scholar
  68. 63.
    Endo, T. et al.: J. Poly. Sci., Polym. Lett. 18, 771 (1980)Google Scholar
  69. 64.
    Goethals, E. J.: Adv. Polym. Sci. 23, 103 (1977)Google Scholar
  70. 65.
    Yamashita, Y., Kawakami, Y., in: Ring-Opening Polymerization, (Ed. T. Saegusa, E. Goethals) Amer. Chem. Soc., Washington, D. C., 1977, p. 99Google Scholar
  71. 66.
    Smis, D.: J. Chem. Soc. 1964, 864Google Scholar
  72. 67.
    Dreyfuss, M. P., Dreyfuss, P.: J. Polym. Sci., Part A-1 4, 2179 (1966)Google Scholar
  73. 68.
    Plesch, P. H., Westermann, P. H.: J. Polym. Sci., Part C 16, 3837 (1968)Google Scholar
  74. 69.
    Yamashita, Y. et al.: Makromol. chem. 114, 146 (1968)Google Scholar
  75. 70.
    Hall, H. K. Jr.: J. Amer. Chem. Soc. 80, 6412 (1958)Google Scholar
  76. 71.
    Dainton, F. S., Ivin, K. J.: Quart. Rev. (London) 12, 61 (1968)Google Scholar
  77. 72.
    Saegusa, T. et al.: Polym. J. 3, 40 (1972)Google Scholar
  78. 73.
    Small, P. A.: Trans. Faraday Soc. 51, 1717 (1955)Google Scholar
  79. 74.
    Okada, M., Mita, K., Sumitomo, H.: Makromol. Chem. 176, 859 (1975)Google Scholar
  80. 75.
    Okada, M., Mita, K., Sumitomo, H.: ibid. 177, 2055 (1976)Google Scholar
  81. 76.
    Cox, J. D.: Tetrahedron 19, 1175 (1963)Google Scholar
  82. 77.
    Greenberg, A, Liebman, J. F.: Strained Organic Molecules, Academic Press, New York, San Francisco and London, 1978Google Scholar
  83. 78.
    Benson, S. W.: Thermochemical Kinetics, John-Wiley & Sons, New York, 1976, p. 60Google Scholar
  84. 79.
    Ref. (26); these data were derived from the Allen bond-energy scheme [Allen, T. L.: J. Chem. Phys. 31, 1039 (L 959)]Google Scholar
  85. 80.
    Cox, J. D., Pilcher, G.: Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York and London, 1970Google Scholar
  86. 81.
    Greenhouse, J. A., Strauss, H. L.: J. Chem. Phys. 50, 124 (1969)Google Scholar
  87. 82.
    Engerholm, G. G. et al.: J. Chem. Phys. 50, 2446 (1969)Google Scholar
  88. 83.
    Cremer, D., Pople, J. A.: J. Amer. Chem. Soc. 97, 1358 (1975)Google Scholar
  89. 84.
    Lemieux, R. U., Stevens, J. D., Fraser, R. R.: Can. J. Chem. 40, 1955 (1962)Google Scholar
  90. 85.
    Gratti, G., Segre, A. L., Morandi, C.: J. Chem. Soc. (13) 1967, 1203Google Scholar
  91. 86.
    Romers, C. et al.: Topics Stereochem. 4, 38 (1969)Google Scholar
  92. 87.
    Riddell, F. G.: Quart. Rev. 21, 364 (1967)Google Scholar
  93. 88.
    Eliel, E. L.: Angew. Chem., Internat. Edn. 11, 739 (1972)Google Scholar
  94. 89.
    De Kok, A. J., Romers, C.: Rec. Trav. Chim. 89, 313 (1970)Google Scholar
  95. 90.
    Nader, F. W.: Tetrahedron Lett. 1975, 1207Google Scholar
  96. 91.
    Nader, F. W.: ibid. 1975, 1591Google Scholar
  97. 92.
    Barbier, C., Delman, J., Rault, J.: ibid. 1964, 3339Google Scholar
  98. 93.
    Anteunis, M., Tavernier, D., Borremans, F.: Bull. Soc. Chim. Belges 75, 396 (1966)Google Scholar
  99. 94.
    Pihlaja, K., Heikkila, J.: Acta Chem. Scand. 21, 2430 (1967)Google Scholar
  100. 95.
    Lambert, J. B.: Acc. Chem. Res. 4, 87 (1971)Google Scholar
  101. 96.
    Forrest, T. P.: J. Amer. Chem. Soc. 97, 2628 (1975)Google Scholar
  102. 97.
    Oyanagi, K. et al.: Bull. Chem. Soc. Japan 48, 751 (1975)Google Scholar
  103. 98.
    Chiang, J. F., Wilcox, C. F. Jr., Bauer, S. H.: J. Amer. Chem. Soc. 90, 3149 (1968)Google Scholar
  104. 99.
    Chiurdoglu, G., (Ed.): Conformational Analysis, Academic Press, New York, London, 1971Google Scholar
  105. 100.
    Hanack, M.: Conformational Theory, Academic Press, New York, 1963Google Scholar
  106. 101.
    McKenna, J.: Conformational Analysis of Organic Compounds, Royal Inst. Chem., Lecture Ser. London, No. 1, 1966Google Scholar
  107. 102.
    Armarego, W. L. F., Gallagher, M. J.: Stereochemistry of Heterocyclic Compounds (Taylor, E. C., Weissberger, A., Ed.), Wiley-Interscience, New York, 1977Google Scholar
  108. 103.
    Packer, W., (Ed.): Saturated Heterocyclic Chemistry, Vol. 1, Chem. Soc., London, 1973Google Scholar
  109. 104.
    Packer, W. (Ed.): ibid., Chem. Soc., London, 1974Google Scholar
  110. 105.
    Ansell, M. F., (Ed.): ibid., Chem. Soc., London, 1975Google Scholar
  111. 106.
    Ansell, M. F., Pattenden, G., (Ed.): ibid., Chem. Soc., London, 1977Google Scholar
  112. 107.
    Pattenden, G., (Ed.): ibid., Chem. Soc., London, 1978Google Scholar
  113. 108.
    Altona, C., Sundaralingam, M.: J. Amer. Chem. Soc. 92, 1995 (1970)Google Scholar
  114. 109.
    Dallinga, G., Toneman, L. H.: Rec. Trav. Chim. 87, 795 (1968)Google Scholar
  115. 110.
    Creswell, R. A.: J. Mol. Spectrosc. 56, 133 (1975)Google Scholar
  116. 111.
    Hall, H. K. Jr., De Blauwe, Fr.: J. Amer. Chem. Soc. 97, 655 (1975)Google Scholar
  117. 112.
    Hall, H. K. Jr., De Blauwe, Fr., Pyriadi, T.: ibid. 97, 3854 (1975)Google Scholar
  118. 113.
    Bouab, O., Moreau, C., Zeh. Ako, M.: Tetrahedron Lett. 1978, 61Google Scholar
  119. 114.
    Bouab, O., Lamaty, G., Moreau, C.: J. Chem. Soc., Chem. Comm. 1978, 678Google Scholar
  120. 115.
    Hendrickson, J. B. et al.: J. Amer. Chem. Soc. 95, 494 (1973)Google Scholar
  121. 116.
    Glazer, E. S. et al.: ibid. 94, 6026 (1972)Google Scholar
  122. 117.
    Engler, E. M., Andose, J. D., Schleyer, P. von R.: ibid. 95, 8005 (1973)Google Scholar
  123. 118.
    Peters, J. A. et al.: Tetrahedron 34, 3313 (1978)Google Scholar
  124. 119.
    Mikhailov, V. K. et al.: Izv. Akad. Nauk. SSSR, Ser. Khim. 11, 2455 (1978); CA 90, 86625 a (1979)Google Scholar
  125. 120.
    Zefirov, N. S., Kurkutova, E. N., Gonchurov, A. V.: Zhur. Org. Khim. 10, 1124 (1974)Google Scholar
  126. 121.
    Goncharov, A. V. et al.: Dokl. Akad. Nauk. SSSR 214, 505 and 810 (1974)Google Scholar
  127. 122.
    Zefirov, N. S. et al.: J. Chem. Soc. Chem. Comm. 1974, 260Google Scholar
  128. 123.
    Zefirov, N. S., Rogozina, S. V.: Tetrahedron 30, 2345 (1974)Google Scholar
  129. 124.
    Gleiter, R. et al.: Dokl. Akad. Nauk, SSSR 235, 347 (1977)Google Scholar
  130. 125.
    Peters, J. A. et al.: Tetradedron Lett. 1979, 2553Google Scholar
  131. 126.
    Swaelens, G., Anteunis, M.: Bull. Soc. Chim. Belges 78, 471 (1969)Google Scholar
  132. 127.
    Anteunis, M., Bécu, C., Anteunis-ole Ketelaere, F.: J. Acta. Crencia Inica 1, 1 (1974)Google Scholar
  133. 128.
    Lemieux, R. U., Chu, N. J.: Abstr. Amer. Chem. Soc. 133, 31 N (1958)Google Scholar
  134. 129.
    Jeffrey, G. A. et al.: J. Amer. Chem. Soc. 100, 373 (1978)Google Scholar
  135. 130.
    Tvaroska, I., Bleha, T.: Can. J. Chem. 57, 424 (1979)Google Scholar
  136. 131.
    Lemieux, R. U.: Pure & Appl. Chem. 25, 527 (1971)Google Scholar
  137. 132.
    De Houg, A. J. et al.: Tetradedron 25, 3365 (1969)Google Scholar
  138. 133.
    Wolfe, S., Whangbo, M.-H., Mitchell, D.: Carbohydr. Res. 69, 1 (1) (1979)Google Scholar
  139. 134.
    Edward, J. T.: Chem. Ind. (London) 1955, 1102Google Scholar
  140. 135.
    Traroška, I., Bleha, T.: Can. J. Chem. 57, 424 (1979)Google Scholar
  141. 136.
    Lucken, E. A. C.: J. Chem. Soc. 1959, 2954Google Scholar
  142. 137.
    Romers, C. et al.: Top. Stereochem. 4, 39 (1969)Google Scholar
  143. 138.
    Baddeley, G.: Tetrahedron Lett. 1973, 1645Google Scholar
  144. 139.
    David, S. et al.: J. Amer. Chem. Soc. 95, 3806 (1973)Google Scholar
  145. 140.
    Bürg, H. B. et al.: Tetrahedron 30, 1563 (1974)Google Scholar
  146. 141.
    Jeffrey, G. A., Pople, J. A., Radom, L.: Carbohydr. Res. 25, 117 (1972)Google Scholar
  147. 142.
    Eliel, E. L., Juaristi, E.: in Ref. (8), pp. 95–106Google Scholar
  148. 143.
    Eliel, E. L., Giza, C. A.: J. Org. Chem. 33, 3754 (1968)Google Scholar
  149. 144.
    Nader, F. W., Eliel, E. L.: J. Amer. Chem. Soc. 92, 3050 (1970)Google Scholar
  150. 145.
    Kaloustian, M. K. et al.: J. Amer. Chem. Soc. 98, 956 (1976)Google Scholar
  151. 146.
    Spelbos, A., Mijlhoff, F. C., Faber, D. H.: J. Mol. Struct. 4, 47 (1977)Google Scholar
  152. 147.
    Gan, T. H., Peel, J. B., Willett, G. D.: Chem. Phys. Lett. 51, 464 (1977)Google Scholar
  153. 148.
    Lee, H., Wilmshurst, J. K.: Spectrochim. Acta. 23A, 247 (1967)Google Scholar
  154. 149.
    Uchida, T., Kurita, Y., Kubo, M.: J. Polym. Sci. 19, 365 (1956)Google Scholar
  155. 150.
    Flory, P. J., Mark, J. E.: Makromol. Chem. 75, 11 (1964)Google Scholar
  156. 151.
    Flory, P. J.: Statistical Mechanics of Chain Molecules, Interscience, New York, 1969Google Scholar
  157. 152.
    Mark, J. E.: Acc. Chem. Res. 7, 218 (1974)Google Scholar
  158. 153.
    Mark, J. E., Flory, P. J.: J. Amer. Chem. Soc. 87, 1415 (1965)Google Scholar
  159. 154.
    Mark, J. E., Flory, P. J.: ibid. 88, 3702 (1966)Google Scholar
  160. 155.
    Bak, K., Elefante, G., Mark, J. E.: J. Phys. Chem. 71, 4007 (1967)Google Scholar
  161. 156.
    Patterson, G. D., Flory, P. J.: J. Chem. Soc., Faraday Trans. 2 68, 1111 (1972)Google Scholar
  162. 157.
    Tadokoro, H. et al.: J. Polym. Sci. 44, 266 (1960)Google Scholar
  163. 158.
    Garazzolo, G.: ibid. A, 1, 1573 (1963)Google Scholar
  164. 159.
    Garazzolo, G., Mammi, M.: ibid. A, 1, 965 (1963)Google Scholar
  165. 160.
    Uchida, T., Tadokoro, H.: ibid. A-2, 5, 63 (1967)Google Scholar
  166. 161.
    Takahashi, Y., Tadokoro, H.: Macromolecules 6, 672 (1973)Google Scholar
  167. 162.
    Takahashi, Y., Sumita, I., Tadokoro, H.: J. Polym. Sci., Polym. Phys. Ed. 11, 2113 (1973)Google Scholar
  168. 163.
    Sasaki, S., Takahashi, Y., Tadokoro, H.: ibid. 10, 2363 (1972)Google Scholar
  169. 164.
    Sasaki, S., Takahashi, Y., Tadokoro, H.: Polym. J. 4, 172 (1973)Google Scholar
  170. 165.
    Mansson, M.: J. Chem. Thermodynamics 1, 141 (1969)Google Scholar
  171. 166.
    Snelson, A., Skinner, H. A.: Trans. Faraday Soc. 57, 2125 (1961)Google Scholar
  172. 167.
    Busfield, W. K., Lee, R. M., Merigold, D.: Makromol. Chem. 156, 183 (1972)Google Scholar
  173. 168.
    Bunn, C. W.: Trans. Faraday Soc. 35, 482 (1939)Google Scholar
  174. 169.
    Mark, J. E.: J. Polym. Sci., Part B 4, 825 (1966)Google Scholar
  175. 170.
    Mark, J. E.: J. Amer. Chem. Soc. 88, 3708 (1966)Google Scholar
  176. 171.
    Abe, A., Mark, J. E.: J. Amer. Chem. Soc. 98, 6468 (1976)Google Scholar
  177. 172.
    Imada, K. et al.: Makromol. Chem. 83, 113 (1965)Google Scholar
  178. 173.
    Cesari, M., Perego, G., Mazzei, A.: ibid. 83, 196 (1965)Google Scholar
  179. 174.
    Angyal, S. K.: Austr. J. Chem. 21, 2737 (1968)Google Scholar
  180. 175.
    Anderson, C. B., Sepp, D. T.: Tetrahedron 24, 1707 (1968)Google Scholar
  181. 176.
    Saegusa, T., Matsumoto, S.: Macromolecules 1, 442 (1968)Google Scholar
  182. 177.
    Saegusa, T., Matsumoto, S.: J. Polym. Sci. Part A-1 6, 1559 (1968)Google Scholar
  183. 178.
    Saegusa, T., Matsumoto, S., Hashimoto, Y.: Macromolecules 4, 1 (1971)Google Scholar
  184. 179.
    Bourdauduca, P., Worsfold, D. J.: ibid. 8, 562 (1975)Google Scholar
  185. 180.
    For example, (a) Saegusa, T., Kobayashi, S.: J. Polym. Sci., Polym. Symp. 56, 241 (1976)Google Scholar
  186. 180. (b)
    Penczek, S., Matyjaszewski, K.: J. Polym. Symp. 56, 255 (1976)Google Scholar
  187. 181.
    Kubisa, P., Penczek, S.: Macromolecules 10, 1216 (1977)CrossRefGoogle Scholar
  188. 182.
    Uryu, T. et al.: Makromol. Chem. 180, 1509 (1979)CrossRefGoogle Scholar
  189. 183.
    Sakharov, A. M. et al.: Dokl. Akad. Nauk. SSSR 250, 1381 (1980); CA 92, 147287 g (1980)Google Scholar
  190. 184.
    Plesch, P. H.: Pure & Appl. Chem. 48, 287 (1967)Google Scholar
  191. 185.
    Penczek, S., Kubisa, P., Matyjaszewski, K.: Adv. Polym. Sci. 37, 1 (1980)Google Scholar
  192. 186. (a)
    Yamashita, Y., Kawakami, Y., Kitano, K.: J. Polym. Sci., Polym. Lett. B 15, 213 (1977)Google Scholar
  193. 186. (b)
    Kawakami, Y., Suzuki, J., Yamashita, Y.: Polym. J. 9, 519 (1977)Google Scholar
  194. 186. (c)
    Kawakami, Y., Yamashita, Y.: Macromolecules 12, 399 (1979); They reported that the polymerization of 1,3,6,9-tetraoxacycloundecane proceeds in two stages, in the first cyclic oligomers are formed via an oxonium ion mechanism and in the second stage high polymers are mainly formed via a carbocation mechanismCrossRefGoogle Scholar
  195. 187.
    Cordes, E. H., Bull, H. G.: Chem. Rev. 74, 581 (1974)Google Scholar
  196. 188.
    Fife, T. H.: Acc. Chem. Res. 8, 264 (1972)Google Scholar
  197. 189.
    Ahmad, M. et al.: J. Amer. Chem. Soc. 101, 2669 (1979)Google Scholar
  198. 190.
    Ramsy, B. C., Taft, R. W.: ibid 88, 3058 (1966)Google Scholar
  199. 191.
    Taft, R. W., Martin, R. H., Lampe, F. W.: ibid. 87, 2490 (1965)Google Scholar
  200. 192.
    Perst, H.: Oxonium Ions in Organic Chemistry, Academic Press, New York, 1971Google Scholar
  201. 193.
    Deslongchamps, P.: Tetrahedron 31, 2463 (1975)Google Scholar
  202. 194.
    Deslongchamps, P. et al.: Can. J. chem. 53, 1601 (1975)Google Scholar
  203. 195.
    Deslongchamps, P.: Heterocycles 7, 1271 (1977)Google Scholar
  204. 196.
    Kirby, A. J., Martin, R. J.: Chem. Commun. 1978, 803Google Scholar
  205. 197.
    Kirby, A. J., Martin, R. J.: ibid. 1979, 1079Google Scholar
  206. 198.
    Wipff, G.: Tetrahedron Lett. 1978, 3269Google Scholar
  207. 199.
    Capozza, R. C., Otten, Gu.: U.S. Pat. 2, 715, 502, Oct., 1977; CA 88, 51358x (1977)Google Scholar
  208. 200.
    Hall, H. K. Jr., Yokoyama, Y.: unpublishedGoogle Scholar
  209. 201.
    Heller, J., Penhale, D. W. H., Helwing, R. F.: J. Polym. Sci., Polym. Lett. 18, 293 (1980)Google Scholar
  210. 202.
    Heller, J., Penhale, D. W. H., Helwing, R. F.: Polym. Preprints 21, No. 2, p. 82, Las Vegas, August, 1980Google Scholar
  211. 203.
    Tvaroska, I., Bleha, T.: Collect. Czech Chem. Commun. 45, 1883 (1980); CA 94, 15031 a (1981); They studied the stability of the (MeO)2CH2 conformer formed by rotation about the central C-O bonds. The anomeric (gauche) effect makes the synclinal more stable than the antiperiplanar conformations. The anomeric effect disappears with increasing solvent polarity. Their results suggest that the anomeric effect still contributes to the stability of the monomer and polymer conformation in polymerization solvents such as dichloromethaneGoogle Scholar

Copyright information

© Springer-Verlag 1982

Authors and Affiliations

  • Y. Yokoyama
    • 1
  • H. K. HallJr.
    • 1
  1. 1.Department of Chemistry, College of Liberal ArtsUniversity of ArizonaTucsonUSA

Personalised recommendations