Monatshefte für Chemie / Chemical Monthly

, Volume 114, Issue 11, pp 1259–1265 | Cite as

Bromination of resin acid derivatives

  • Ernst Haslinger
  • Hermann Kalchhauser
  • Harald Steindl
Organische Chemie Und Biochemie

Abstract

Radicalic bromination of1,2, and3 leads to products with halogen in the isopropyl group. The corresponding olefins are obtained by elimination of HBr.

Keywords

17,19-Dinoratis-15-ene-4,13,14-tricarboxylic acid, 16-(1-methylethyl), cyclic-13,14-anhydride (4α,8α,12α) and derivatives 17,19-Dinoratis-15-ene-4,13,14-tricarboxylic acid, 16-(1-methylethyl), 4,13,14-trimethylester (4α,8α,12α,13β,14α) and derivatives 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-, [1R-(1α,4aα,4bβ,10aα)] and derivatives 

Bromierung von Harzsäurederivaten

Zusammenfassung

Die radikalische Bromierung von1,2 und3 führt zu in der Seitenkette halogenierten Produkten. Eliminierung von HBr liefert die entsprechenden Olefine.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Zeiss H. H., Martin W. B. jr., J. Amer. Chem. Soc.75, 5935 (1953).Google Scholar
  2. 2.
    Huffman J. W., Stockel R. F., J. Org. Chem.28, 506 (1963).Google Scholar
  3. 3.
    Huffman J. W., Arapakos P. G., J. Org. Chem.30, 1604 (1965).Google Scholar
  4. 4.
    Bennett C. R., Cambie R. C., Fullerton T. J., Aust. J. Chem.21, 2473 (1968).Google Scholar
  5. 5.
    Cambie R. C., Denny W. A., Aust. J. Chem.22, 1699 (1969).Google Scholar
  6. 6.
    Pettit G. R., Dias J. R., Can. J. Chem.47, 1091 (1969).Google Scholar
  7. 7.
    Huffman J. W., J. Org. Chem.35, 478 (1970).Google Scholar
  8. 8.
    Cambie R. C., Franich R. A., Aust. J. Chem.23, 93 (1970);24, 117 (1971);24, 217 (1971).Google Scholar
  9. 9.
    Wirthlin T., Wehrli H., Jeger O., Helv. Chim. Acta57, 351 (1974).Google Scholar
  10. 10.
    Tahara A.,Shimagaki M., Chem. Lett.1974, 651.Google Scholar
  11. 11.
    Tahara A., Akita H., Ohtsuka Y., Chem. Pharm. Bull.22, 1547 (1974).Google Scholar
  12. 12.
    Tahara A., Shimagaki M., Itoh M., Harigaya Y., Onda M., Chem. Pharm. Bull.23, 3189 (1975).Google Scholar
  13. 13.
    Tahara A., Harigaya Y., Onda M., Chem. Pharm. Bull.23, 1989 (1975);23, 1996 (1975);24, 421 (1976).Google Scholar
  14. 14.
    Ritchie P. F., J. Amer. Chem. Soc.76, 723 (1954).Google Scholar
  15. 15.
    Sanderson T. F., U.S. Patent 2750367 (1956); cf. C.A.51, 1278c (1957).Google Scholar
  16. 16.
    Ohta M., Ohmori L., Chem. Pharm. Bull.5, 91 (1957).Google Scholar
  17. 17.
    Tahara A., Akita H., Chem. Pharm. Bull.23, 1984 (1975).Google Scholar
  18. 18.
    Tahara A., Chem. Pharm. Bull.24, 1497 (1976).Google Scholar
  19. 19.
    Ayer W. A., McDonald C. E., Stothers J. B., Can. J. Chem.41, 1113 (1963).Google Scholar
  20. 20.
    Halbrook N. J., Lawrence R. V., Dressler R. L., Blackstone R. C., Herz W., J. Org. Chem.29, 1017 (1964).Google Scholar
  21. 21.
    Maciejewski C., Gastambide B., Helv. Chim. Acta60, 524 (1977) and refs. cited therein.Google Scholar
  22. 22.
    Haslinger E., Kalchhauser H., Robien W., Monatsh. Chem.113, 805 (1982).Google Scholar
  23. 23.
    Zalkow L. H., Ford R. A., Kutney J. P., J. Org. Chem.27, 3535 (1962).Google Scholar
  24. 24.
    Huffman R. W., Diss. Abstr.B 25, 6232 (1965).Google Scholar
  25. 25.
    Maciejewski C., Gastambide B., Chimia31, 8 (1977).Google Scholar
  26. 26.
    Herz W., Mirrington R. N., Young H., Yen Lin Young, J. Org. Chem.33, 4210 (1968).Google Scholar
  27. 27.
    Langlois N.,Gastambide B., Bull. Soc. Chim. France1965, 2966.Google Scholar
  28. 28.
    Blade-Font A., Rocabayera T. d. m., Salomo S. A., Afinidad28 (292), 1301 (1971).Google Scholar
  29. 29.
    Fleck E. E., Palkin S., J. Amer. Chem. Soc.60, 921 (1938).Google Scholar
  30. 30.
    Skell P. S., Tuleen D. L., Readio P. D., J. Amer. Chem. Soc.85, 2849 (1963).Google Scholar
  31. 31.
    Cava M. P., Krieger M., Pohlke R., Mangold D., J. Amer. Chem. Soc.88, 2615 (1966).Google Scholar

Copyright information

© Springer-Verlag 1983

Authors and Affiliations

  • Ernst Haslinger
    • 1
  • Hermann Kalchhauser
    • 1
  • Harald Steindl
    • 1
  1. 1.Institut für Organische ChemieUniversität WienWienAustria

Personalised recommendations