Optically Active Poly-Propiothiolactones

  • Dragutin Fles
Part of the Charged and Reactive Polymers book series (CHRP, volume 5)


A review of the work which concerns the preparation and properties of polythiolesters prepared by ring opening polymerization of propiothiolactones is presented in this article. The major part deals with the mechanism of polymerization of optically active α-substituted-β-thiolactones and specially with the study of polymerizability with respect to the character of α-substituent. Three types of monomer were used in the polymerization reactions: para-substituted benzenesulfonamido-β-thiolactones in which the para substituents are OMe, Me, H, C1, and NO2, group, N-disubstituted-amino-β- thiolactones and α-methyl-α-ethyl-β-thiolactone. The general conclusion of our work on the polymerization of α-substituted β-thiolactones is that the rate of polymerization is very much affected by the character of α-substituent, and that the hydrogen bonding in α-acylamino-β-thiolactones plays an important role in the ring opening and propagation of the polymerization reactions.


Polymerization Reaction Specific Rotation Ethyl Chloroformate Hydriodic Acid Active Poly 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Lin’kova, M. G., Kil’dijheva, O. V.. and Knunyants, I. L.: lzvest. Akad. Nauk S.S.S.R.. Otdel. Khim Nauk 569 (1955).Google Scholar
  2. 2.
    Etienne. Y. and Fischer. N.: in A. Weissberger (ed.), β-actones in the series of monographs: The Chemistry of Heterocyclic Compounds, Intcrsckncc Publishers. New York. 1964. Vol. 19. pp. 729–883.Google Scholar
  3. 3.
    Fles, D., Markovac-Prpic, A., and Tomasic. V.: J. Am. Chem. Soc. 80, 4654 (1958).CrossRefGoogle Scholar
  4. 4.
    Sweeney, W and Casey. D. J. (E.L du Pont de Nemours and Co.): U.S. 3 367 921. Feb. 6, 1968.Google Scholar
  5. 5.
    Fles, D. and Tomasic, V.: Polym. Lett. 6. 809 (1969).CrossRefGoogle Scholar
  6. 6.
    Fles. D., Tomasic, V., Sainsa. M.. Ahmetovic, D., Jerman, B., and Fles Mclita: J. Polymer Sci. Symp. 42. 321 (1973).CrossRefGoogle Scholar
  7. 7.
    Jerman. B. and Ftov. D.: J. Polymer Sci. Polym. Chem Ed 14, 1117 (1976).Google Scholar
  8. 8.
    Knunyants. I. L.. Kil’dishcva, O. V.. and Petrova. E.: Izvett. Akad. Nauk S.S.S.R. Otdel-Khim. Nauk 689 (1955).Google Scholar
  9. 9.
    Shcchan. J. C.: Ann. N. Y. Acad. Sci. 88. 665 (I960).Google Scholar
  10. 10.
    Dadic, M., Fles, D., and Markovac-Prpic, A.: Croat. Chem. Acta 33. 73 (1961).Google Scholar
  11. 11.
    Fles, D.. Tomasic. V.. and Jankovic. A.: unpublished results.Google Scholar
  12. 12.
    Fles. D., Ahmetovic, D, and Tomasic, V.: XXIII International Symposium on Macroinolccules, Madrid. Sept. 1974, Preprint 1, pp. 5–12.Google Scholar
  13. 13.
    Freudenbern, K. and Hotmann, W.: Ann 584, 54 (1953).Google Scholar
  14. 14.
    Milinovic, I., Bezjak, A., and Fles, D.: Croat. Chem. Acta 45, 551 (1973).Google Scholar
  15. 15.
    Outani, Y., Uchida, T.. and Tadokoro. H.: J. MacromoL Sci.. Phys. B2. 567 (1968).CrossRefGoogle Scholar
  16. 16.
    Knunyants, I. L., Kil’disheva, O. V., and Pervova, E. J.: Izvest. Akad. Nauk S.S.S.R., Otdel. Khim Nauk 696. (1955).Google Scholar
  17. 17.
    Knunyants, I.L., Pen-Ova, E. J., and Lin’kova, M. G.: Khim. Nauka Prom. 3. 278 (1958).Google Scholar
  18. 18.
    Fles. D.. Markovac-Prpic, A., Tomasic, V.. and Milohnoja, M.: Croat. Chem. Acta 30. 167 (1958).Google Scholar
  19. 19.
    Grttham,T. L: Brit. 648 886(195l); Chem. Abstr. 45. 8031 (1951).Google Scholar
  20. 20.
    Grcsham, T. L.. Jarnen, J. E., Shaver, F. W„ Bankert. R. A., and Ficdorek, F. T.: J. Am. Chem. Soc. 73. 3618 (1951).Google Scholar
  21. 21.
    Knunyants. I. L.. Lin’kova. M. G„ and Kulesova, N. D.: Izvet Akad. Nauk S.S.S.R, Otdel. Khim. Nauk 664(1964).Google Scholar
  22. 22.
    B. F. Goodrich Co.: Brit. 840658. July 6. 1960.Google Scholar
  23. 23.
    Knunyants. L I… Kulesova, N. D., ami Lin’kova, M. G.: Izrest. Akad. Nauk S.S.S.R.. Otdel. Khim. Nauk 1081 (1965).Google Scholar
  24. 24.
    Krilov. D.. Vcksli. 2.. and lies. D.: J. Polymer Sci.. Polym Chem. Ed. 14. 777 (1976).Google Scholar
  25. 25.
    Fles. M.: Bull. Sci ConteiL Akad. RSF Yougostovie 17. 146 (1972).Google Scholar

Copyright information

© D. Reidel Publishing Company 1979

Authors and Affiliations

  • Dragutin Fles
    • 1
  1. 1.Research and Development Institute INAZagrebYugoslavia

Personalised recommendations