Skip to main content
SpringerLink
Log in

Optically Active Vinyl Polymers with Backbone Chirality

  • Chapter
Recent Advances in Mechanistic and Synthetic Aspects of Polymerization

Part of the book series: NATO ASI Series ((ASIC,volume 215))

  • 175 Accesses

Abstract

By symmetry considerations it was found that certain stereochemical arrangements of vinyl monomers in homo- and copolymers would exhibit main chain chirality and hence should show optical activity. Several possible theoretical cases are discussed.

By an asymmetric cyclocopolymerization copolymers showing optical activity due to chirality of the backbone could be realized. The mechanism of this reaction was investigated.

Another possibility for obtaining optically active vinyl or vinylidene polymers is due to a chiral helical conformation stabilized by bulky substituents.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. N. Beredjick, C. Schuerch, J. Am. Chem. Soc. 80 (1958) 1933.

    Article  CAS  Google Scholar 

  2. G. Natta, M. Farina, M. Peraldo, G. Bressan, Makromol. Chem. 43 (1961) 68.

    Article  CAS  Google Scholar 

  3. M. Farina, M. Peraldo, G. Natta, Angew. Chem. 77 (1965) 149.

    Article  CAS  Google Scholar 

  4. For reviews on optically active polymers see: C.L. Arcus, Prog. Stereochem. 3 (1962) 264; R.C. Schulz, E. Kaiser, Adv. Polym. Sci. 4 (1965) 236; P. Pino, Ibid. 4 (1965) 393; M. Farina, G. Bressan, Stereochem. Macromol. 3 (1967) 181; E. Selegny, Ed. Optically Active Polymers; D. Reidel Publishing Comp.: Dordrecht, Holland 1979; P. Pino, G.P. Lorenzi, in:Preparation and Properties of Stereoregular Polymers, R.W. Lenz, F. Ciardelli, Eds.; D. Reidel Publishing Comp.: Dordrecht, Holland, 1980. Chapter 1.

    CAS  Google Scholar 

  5. G. Natta, M. Farina, M. Donati, M. Peraldo, Chim. Ind. (Milan) 42 (1960) 1363.

    CAS  Google Scholar 

  6. For reviews on the stereochemistry of vinyl polymers see: A.D. Ketley, Ed. The Stereochemistry of Macromolecules. 3 Volumes, M. Dekker, New York, 1967-1968; F.A. Bovey, Polymer Conformation and Configuration, Academic Press, New York, 1969; R.W. Lenz and F. Ciardelli, Eds., Preparation and Properties of Stereoregular Polymers, D. Reidel Publishing Comp, Dordrecht, Holland, 1980.

    Google Scholar 

  7. H. Staudinger, Die hochmolekularen, organischen Verbindungen, J. Springer, Berlin, 1932, pp. 113–114.

    Google Scholar 

  8. F. Ciardelli, P. Salvadori, Pure Appl. Chem. 57, (1985) 931.

    Article  CAS  Google Scholar 

  9. M.M. Green, B.A. Garetz, Tetrahedron Lett. 25, (1984) 2831.

    Article  CAS  Google Scholar 

  10. C.L. Arcus, J. Chem. Soc. 1957, 1189.

    Google Scholar 

  11. G. Wulff, A. Sarhan, K. Zabrocki, Tetrahedron Lett. 1973, 4329; G. Wulff, W. Vesper, R. Grobe-Einsler, A. Sarhan, Makromol. Chem. 178, (1977) 2799.

    Google Scholar 

  12. For a review see: G. Wulff, in: W.T. Ford, Ed., Polymeric Reagents and Catalysts, ACS-Symposium Series, 308, 1986, p. 186.

    Chapter  Google Scholar 

  13. G. Wulff, K. Zabrocki, J. Hohn, Angew. Chem. 90, (1978) 567; Angew. Chem. Int. Ed. Engl. 17, (1978) 535.

    Article  CAS  Google Scholar 

  14. G. Wulff, J. Hohn, Macromolecules, 5 (1982) 1255.

    Article  Google Scholar 

  15. For a short review see: G. Wulff, Nachr. Chem. Techn. Lab. 33 (1985) 956.

    Article  CAS  Google Scholar 

  16. Y. Okamoto, K. Suzuki, K. Ohta, K. Hatada, H. Yuki, J. Am. Chem. Soc. 101 (1979) 4763.

    Article  CAS  Google Scholar 

  17. Y. Okamoto, K. Ohta, K. Hatada, H. Yuki, in: Anionic Polymerization: Kinetics, Mechanism and Synthesis, J.E. McGrath, Ed., ACS-Symposium Series 166, 1981, p. 353.

    Google Scholar 

  18. G. Wulff, R. Sczepan, A. Steigel, Tetrahedron Lett. 27 (1986) 1991.

    Article  CAS  Google Scholar 

  19. D.J. Cram, D.Y. Sogah, J. Am. Chem. Soc. 107 (1985) 8301.

    Article  CAS  Google Scholar 

  20. W. Kaminsky, S. Niedoba, presented at the Makromolekulares Kolloquium, Freiburg, March 1986 in Freiburg, F.R.G.; Abstract page 33.

    Google Scholar 

  21. W.J. Harris, O. Vogl, J.R. Havens, J.L. Koenig, Makromol. Chem. 184 (1983) 1243 and earlier papers.

    Article  CAS  Google Scholar 

  22. J.M. Van der Eijk, V.E.M. Richters, R.J.M. Nolte, W. Drenth, Recl. Trav. Chim. Pays-Bas 103 (1984) 46 and earlier papers.

    Article  Google Scholar 

  23. G. Wulff, R. Kemmerer, J. Vietmeier, H.-G. Poll, Nouv. J. Chim. 6 (1982) 681.

    CAS  Google Scholar 

  24. G. Wulff, R. Kemmerer, P.K. Dhal, A. Steigel, Manuscript under preparation.

    Google Scholar 

  25. G. Wulff, R. Kemmerer, B. Vogt, Manuscript under preparation.

    Google Scholar 

  26. see e.g.: G.B. Butler, J. Polym. Sei. Polym. Symp. 64 (1978) 71.

    Article  CAS  Google Scholar 

  27. G. Wulff, R. Kemmerer, B. Vogt, presented at the Makromolekulares Kolloquium, March 1986 in Freiburg, F.R.G., Abstract page 31.

    Google Scholar 

  28. P.K. Dhal, G. Wulff, Manuscript under preparation.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry II, University of Düsseldorf, Universitätsstr. 1, D-4000, Düsseldorf 1, Federal Republic of Germany

    Günter Wulff

Authors
  1. Günter Wulff
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. University of Bordeaux I, Talence, France

    M. Fontanille

  2. C.N.R.S. - Laboratory of Organic Materials, Lyon-Vernaison, France

    A. Guyot

Rights and permissions

Reprints and permissions

Copyright information

© 1987 D. Reidel Publishing Company

About this chapter

Cite this chapter

Wulff, G. (1987). Optically Active Vinyl Polymers with Backbone Chirality. In: Fontanille, M., Guyot, A. (eds) Recent Advances in Mechanistic and Synthetic Aspects of Polymerization. NATO ASI Series, vol 215. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-3989-9_32

Download citation

  • DOI: https://doi.org/10.1007/978-94-009-3989-9_32

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-8270-9

  • Online ISBN: 978-94-009-3989-9

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation