Skip to main content
SpringerLink
Log in

The labile stereochemistry of conjugated systems

  • Informationen
  • Studiorum Progressus
  • Published:
Experientia Aims and scope Submit manuscript

Zusammenfassung

Die Faktoren, welche die labile Stereochemie von konjugierten Systemen beeinflussen, werden diskutiert. Das Studium der Elektronenspektren solcher Systeme zeigt, dass in vielen Fällen Moleküle, welche in vorwiegend unebenen (nichtplanaren) Grundzuständen existieren, in vorwiegend ebene (planare) erregte Zustände übergehen. Die Gleichgewichtskonstellationen werden abgeleitet für Biphenylderivate, Arylketone, Styrole, Arylamine, Cyclohexenderivate und cyclische und acyclische Diene.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. J. Dhar, Proc. Nat. Inst. Sci. India15, 11 (1949).

    CAS  Google Scholar 

  2. O. Bastiansen, Acta Chem. Scand.3, 408 (1949).

    Article  CAS  Google Scholar 

  3. SeeR. Adams andH. C. Yuan, Chem. Reviews12, 261 (1933).

    Article  CAS  Google Scholar 

  4. L. W. Pickett, G. F. Walter, andH. France, J. Amer. Chem. Soc.58, 2296 (1936).

    Article  CAS  Google Scholar 

  5. SeeE. A. Braude andE. S. Waight in “Progress in Stereochemistry” (W. Klyne, Ed.), Vol. 1., Chapter 4 (Butterworths, London 1954), for a summary of data and literature references.

    Google Scholar 

  6. E. A. Braude, F. Sondheimer, andW. F. Forbes, Nature173, 117 (1954), and forthcoming papers in J. Chem. Soc.

    Article  CAS  Google Scholar 

  7. E. A. Braude, F. Sondheimer, andW. F. Forbes, Nature173, 117 (1954), and forthcoming papers in J. Chem. Soc.

    Article  CAS  Google Scholar 

  8. Unless otherwise stated, the data in this and the following tables are taken fromE. A. Braude andE. S. Waight, “Progress in Stereochemistry” (W. Klyne, Ed.), Vol. 1., Chapter 4 (Butterworths, London, 1954), andE. A. Braude, F. Sondheimer, andW. F. Forbes, Nature173, 117 (1954), and forthcoming papers in J. Chem. Soc.

    Google Scholar 

  9. E. A. Braude andE. S. Waight, “Progress in Stereochemistry” (W. Klyne, Ed.). Vol. 1., Chapter 4 (Butterworths, London 1954), andE. A. Braude, F. Sondheimer, andW. F. Forbes, Nature173, 117 (1954) used a cosΘ function. The cos2 Θ function is more satisfactory because it has the value 1 forΘ=0 and 180°, as well as from other theoretical considerations.

    Google Scholar 

  10. G. H. Beaven, D. M. Hall, M. S. Lesslie, andE. E. Turner, J. Chem. Soc.1952, 854.

  11. G. H. Beaven, D. M. Hall, M. S. Lesslie, E. E. Turner, andG. R. Bird, J. Chem. Soc.1954, 131.

  12. D. M Hall, S. Ridgwell, andE. E. Turner, J. Chem. Soc.1954, 2498.

  13. E. A. Braude, F. Sondheimer, andW. F. Forbes, Nature173, 117 (1954), and forthcoming papers in J. Chem. Soc.

    Article  CAS  Google Scholar 

  14. M. T. O'Shaughnessy andW. H. Rodebush, J. Amer. Chem. Soc.62, 2906 (1940).

    Article  CAS  Google Scholar 

  15. E. A. Braude, F. Sondheimer, andW. F. Forbes, Nature173, 117 (1954), and forthcoming papers in J. Chem. Soc.

    Article  CAS  Google Scholar 

  16. J. B. Bentley, K. B. Everard, R. J. B. Marsden, andL. E. Sutton, J. Chem. Soc.1949, 2957.

  17. E. A. Braude, J. S. Fawcett, andD. D. E. Newman, J. Chem. Soc.1950, 793.

  18. W. R. Remington, J. Amer. Chem. Soc.67, 1838 (1945).

    Article  CAS  Google Scholar 

  19. H. B. Klevens andJ. R. Platt, J. Amer. Chem. Soc.71, 1714 (1949).

    Article  CAS  Google Scholar 

  20. V. Prelog andP. Wieland, Helv. Chim. Acta27, 1127 (1944).

    Article  CAS  Google Scholar 

  21. B. M. Wepster, Rec. Trav. Chim. Pays-Bas72, 662 (1953).

    Google Scholar 

  22. E. A. Braude, E. R. H. Jones, H. P. Koch, R. W. Richardson, F. Sondheimer, andB. J. Toogood, J. Chem. Soc.1949, 1890.

  23. R. B. Turner andD. M. Voitle, J. Amer. Chem. Soc.73, 1403 (1951).

    Article  CAS  Google Scholar 

  24. E. A. Braude, E. R. H. Jones, H. P. Koch, R. W. Richardson, F. Sondheimer, andJ. B. Toogood, J. Chem. Soc.1949, 1890.

  25. E. A. Braude andE. R. H. Jones, J. Amer. Chem. Soc.72, 1041 (1950).

    Article  CAS  Google Scholar 

  26. C. H. MacGillavry, A. Kreuger, andE. L. Eichhorn, Proc. Acad. Sci. Amst.B54, 449 (1951), and private communication from ProfessorMacGillavry.

    Google Scholar 

  27. E. A. Braude et al., loc. cit.

    Article  CAS  Google Scholar 

  28. R. S. Mulliken, J. Chem. Physics7, 121 (1939).

    Article  CAS  Google Scholar 

  29. J. G. Aston, G. Szasz, H. W. Wooley, andF. G. Brickwedde, J. Chem. Physics14, 67 (1946).

    Article  CAS  Google Scholar 

  30. V. Schomaker andL. Pauling, J. Amer. Chem. Soc.61, 1769 (1939).

    Article  CAS  Google Scholar 

  31. K. Bradacs andL. Kahovec, Z. physikal. Chem.B48, 635 (1940).

    Google Scholar 

  32. G. J. Szasz andN. Sheppard, Trans. Faraday Soc.49, 358 (1953).

    Article  CAS  Google Scholar 

  33. E. A. Braude, Chem. and Industry1954, 1557.

  34. In a recent paper,A. T. Blomquist andA. Goldstein [J. Amer. Chem. Soc.77, 998 (1955)] have described thecis-cis-isomer ofcyclodeca-1:3-diene which showsno band in the 2150–2300 Å region, indicating that the diene system in this isomer is highly non-planar.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Imperial College of Science and Technology, South Kensington, S.W.7, London

    E. A. Braude

Authors
  1. E. A. Braude
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Summary of a lecture delivered at the Eidgenössische Technische Hochschule, Zürich, on January 24, 1955.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Braude, E.A. The labile stereochemistry of conjugated systems. Experientia 11, 457–464 (1955). https://doi.org/10.1007/BF02172561

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02172561

Search

Navigation