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Diisophorone and related compounds. Part 12 Synthesis of 4-bromodiisophorones and their reactions with nucleophiles

Diisophoron und verwandte Verbindungen, 12. Mitt.: Synthese von 4-Bromdiisophoronen und ihre Reaktion mit Nucleophilen

  • Organische Chemie Und Biochemie
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Abstract

4-Bromodiisophor-2(7)-en-1-ol-3-one (2) is accessible by the action of hydrobromic acid on 2,7-epoxydiisophoran-1-ol-3-one (1), and is convertible into the corresponding 1-carboxylic acid (9) by theKoch-Haaf reaction. Nucleophilic substitution displaces the halogen in both the 4-bromoketol (2) and the 4-bromoketo-acid (9). Amongst the products thus obtained, 4-hydroxy-1-carboxydiisophor-2(7)-en-3-one (11) is of special interest as a source of the 3,4-diketo-1-carboxylic acid (13).

Zusammenfassung

4-Bromdiisophor-2(7)-en-1-ol-3-on (2) ist durch Einwirkung von Bromwasserstoffsäure auf 2,7-Epoxydiisophoran-1-ol-3-on (1) erhältlich und wird mittels derKoch-Haaf-Reaktion zur entsprechenden 1-Carbonsäure (9) umgesetzt. Durch nucleophile Reagenzien wird das Halogen sowohl im 4-Bromketol (2) als auch in der 4-Bromoketosäure (9) substituiert. Unter den so erhältlichen Produkten ist das 4-Hydroxy-1-carboxydiisophor-2(7)-en-3-on als Ausgangsmaterial für die 3,4-Diketo-1-säure (13) von zusätzlichem Interesse.

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References

  1. Part 11:Kurzer F., Morgan A. R., Rettig S. J., Monatsh. Chem.115, 333 (1984).

    Article  CAS  Google Scholar 

  2. Allen A. A., Duffner C. R., Kurzer F., Tetrahedron34, 1247 (1978).

    Article  CAS  Google Scholar 

  3. Kabas G., Rutz H. C., Tetrahedron22, 1219 (1966).

    Article  CAS  Google Scholar 

  4. Furth B.,Kossanyi J.,Morizur J. P.,Vandewalle M., Bull. Soc. chim. France1967, 1428.

  5. Duffner C. R., Kurzer F., Tetrahedron34, 1251 (1978).

    Article  CAS  Google Scholar 

  6. Allen A. A., Kurzer F., Monatsh. Chem.112, 617 (1981).

    Article  CAS  Google Scholar 

  7. Davies P. R., Kurzer F., Morgan A. R., Monatsh. Chem.111, 1097 (1980).

    Article  CAS  Google Scholar 

  8. Kurzer F., Morgan A. R., Monatsh. Chem.112, 129 (1981).

    Article  CAS  Google Scholar 

  9. Allen A. A., Kurzer F., Monatsh. Chem.112, 769 (1981).

    Article  CAS  Google Scholar 

  10. Allen A. A.,Kurzer F.,Morgan A. R., J.C.S. Perkin I1980, 733.

  11. Allen A. A., Kurzer F., Tetrahedron34, 1261 (1978).

    Article  CAS  Google Scholar 

  12. Rosowsky A., Heterocyclic Compounds with Three of Four Membered Rings (Weissberger A., ed.), Part I, pp. 270, 273, 350, 366. New York: Interscience. 1964.

    Google Scholar 

  13. Winstein S., Henderson R. B., Heterocyclic Compounds (Elderfield R. C., ed.), Vol. I, p. 1. New York: Wiley. 1950.

    Google Scholar 

  14. Kossanyi J.,Morizur J. P.,Furth B.,Vandewalle M., Bull. Soc. chim. France1967, 2180.

  15. Davies P. R., Morgan A. R., Kurzer F., Monatsh. Chem.114, 739 (1983).

    Article  CAS  Google Scholar 

  16. Parker R. E., Isaacs N. S., Chem. Rev.59, 737 (1959).

    Article  CAS  Google Scholar 

  17. Koch H., Haaf W., Liebig's Ann.618, 251 (1958); ibid.638, 111, 122 (1960); Org. Synth.44, 1 (1964); Coll. Vol.5, 20 (1973).

    Article  CAS  Google Scholar 

  18. Stetter H., Schwarz M., Hirschhorn A., Chem. Ber.92, 1629 (1959);Stetter H., Mayer J., Schwarz M., Wulff C., ibid.93, 226 (1960);Stetter H., Wulff C., ibid.93, 1366 (1960).

    Article  CAS  Google Scholar 

  19. Fieser L. F.,Fieser M., Reagents for Organic Synthesis Vol. 1, p. 144 (1967);

  20. Vol. 1, p. 191 (1967); Vol. 2, p. 102 (1969), and references given therein. New York: Wiley.

  21. Allen A. A., Kurzer F., Tetrahedron34, 1267 (1978).

    Article  CAS  Google Scholar 

  22. Fischer E., Speier A., Ber. dtsch. chem. Ges.28, 3252 (1895).

    Article  CAS  Google Scholar 

  23. Prelog V., Seiwerth R., Ber. dtsch. chem. Ges.74, 1644 (1941);Stetter H., Bänder O. E., Chem. Ber.88, 1535 (1955).

    Article  Google Scholar 

  24. Kindler K., Ber. dtsch. chem. Ges.69, 2792 (1936).

    Article  Google Scholar 

  25. Gutsche C. D., Organic Reactions8, 364, 377 (1954).

    Google Scholar 

Download references

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Authors and Affiliations

  1. Royal Free Hospital School of Medicine, University of London, London, England

    Frederick Kurzer & Jayantilal N. Patel

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  1. Frederick Kurzer
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  2. Jayantilal N. Patel
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Kurzer, F., Patel, J.N. Diisophorone and related compounds. Part 12 Synthesis of 4-bromodiisophorones and their reactions with nucleophiles. Monatsh Chem 115, 793–807 (1984). https://doi.org/10.1007/BF01120976

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  • DOI: https://doi.org/10.1007/BF01120976

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