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Monatshefte für Chemie / Chemical Monthly

, Volume 108, Issue 4, pp 803–811 | Cite as

Hydroxybromierung und Methoxybromierung von (Z)-Cycloocten

  • Günter Haufe
  • Manfred Mühlstädt
  • Jürgen Graefe
Organische Chemie und Biochemie

Hydroxybromination and methoxybromination of (Z)-cyclooctene

Abstract

In addition totrans-2-bromocyclooctanol andtrans-1,2-dibromocyclooctane,cis-4-bromocyclooctanol,cis-1,4-dibromocyclooctane,trans-1,4-dibromocyclooctane, and (Z)-5-bromocyclooctene are obtained, when (Z)-cyclooctene is treated with N-bromosuccinimide in the presence of water. Similarly the methoxybromination of (Z)-cyclooctene gives transanular products.

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Literatur

  1. 1.
    Aus der Dissertation zur Promotion A vonG. Haufe, Karl Marx-Universität Leipzig, 1975.Google Scholar
  2. 2.
    C. O. Guss undR. Rosenthal, J. Amer. Chem. Soc.77, 2549 (1955).Google Scholar
  3. 3.
    H. S. Golinkin, D. M. Parbhoo undR. E. Robertson, Canad. J. Chem.48, 1296 (1970).Google Scholar
  4. 4.
    A. Jovtscheff, Izvest. Inst. org. Chim. bulgarska Akad. Naukite2, 67 (1965); Chem. Abstr.64, 11075 h (1966).Google Scholar
  5. 5.
    A. Bresson, G. Dauphin, J. M. Geneste, A. Kergomard undA. Lacourt, Bull. Soc. chim. France1970, 2432.Google Scholar
  6. 6.
    G. Haufe, M. Mühlstädt undJ. Graefe, Mh. Chem.107, 653 (1976).Google Scholar
  7. 7 a).
    M. Mousseron, Bull. Soc. chim. France51, 782 (1932);Google Scholar
  8. 7 b).
    M. Godchot, M. Mousseron undR. Granger, C.r. hebdomad. Sé. Acad. Sci.200, 748 (1935)Google Scholar
  9. 7 c).
    M. Mousseron, G. Combes undF. Winternitz, Bull. Soc. chim. France1946, 616.Google Scholar
  10. 8.
    P. W. Henniger, L. J. Dukker undE. Havinga, Rec. Trav. Chim. Pays-bas85, 1177 (1966).Google Scholar
  11. 9.
    A. C. Cope undH. E. Johnson, J. Amer. Chem. Soc.79, 3889 (1957).Google Scholar
  12. 10.
    M. Godchot undG. Canquil, C. r. hebdomad. Sé. Acad. Sci.192, 962 (1931).Google Scholar
  13. 11.
    G. Berti, in Topics in Stereochemistry (N. L. Allinger undE. L. Eliel, Hrsg.), Bd. 7, S. 93ff. New York-London-Sydney-Toronto: Interscience. 1973.Google Scholar
  14. 12.
    P. D. Bartlett, J. Amer. Chem. Soc.57, 224 (1935).Google Scholar
  15. 13.
    J. Steigman undL. P. Hammett, J. Amer. Chem. Soc.59, 2536 (1937).Google Scholar
  16. 14.
    A. C. Cope undB. C. Anderson, J. Amer. Chem. Soc.79, 3892 (1957).Google Scholar
  17. 15.
    A. C. Cope, A. H. Keough, P. E. Peterson, H. E. Simmons undG. W. Wood, J. Amer. Chem. Soc.79, 3900 (1957).Google Scholar
  18. 16.
    I. D. Roberts, W. G. Young undS. Winstein, J. Amer. Chem. Soc.64, 2157 (1942).Google Scholar
  19. 17.
    L. N. Owen undP. N. Smith, J. Chem. Soc. [London]1952, 4035.Google Scholar
  20. 18.
    H. J. Franz, W. Höbold, R. Höhn G. Müller-Hagen, R. Müller, W. Pritzkow undH. Schmidt, J. prakt. Chem.312, 622 (1970).Google Scholar
  21. 19.
    M. S. Baird, C. B. Reese undM. R. D. Stebles, Chem. Commun.1971, 1340.Google Scholar
  22. 20.
    A. C. Cope, M. M. Martin undM. A. McKervey, Quart. Reviews Chem. Soc.20, 119 (1969) und dort zitierte Arbeiten.Google Scholar
  23. 21.
    K. Ziegler undH. Wilms, Ann. Chem.567, 1 (1950).Google Scholar

Copyright information

© Springer-Verlag 1977

Authors and Affiliations

  • Günter Haufe
    • 1
  • Manfred Mühlstädt
    • 1
  • Jürgen Graefe
    • 2
  1. 1.Sektion ChemieKarl-Marx-Universität LeipzigDeutsche Demokratische Republik
  2. 2.Sektion ChemieFriedrich-Schiller-Universität JenaJenaDeutsche Demokratische Republik

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