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Aromatische Spirane, 16. Mitt.: Darstellung von monound dianellierten 2,2′-Spirobiindan-1,1′-dionen

Aromatic spiranes, XVI: Syntheses of mono- and dianellated 2,2′-spirobiindane-1,1′-diones

  • Organische Chemie Und Biochemie
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Summary

The spiroketones19, 21, 24, 27, and31 were prepared by cyclisation of the dicarboxylic acids and their acid chlorides, resp., (18, 20, 22, 23, 25, 26, 28, and30) with polyphosphoric acid (PPA) or SnCl4. The latter compounds were synthesized by alkylation of the appropriate β-keto esters10, 11, 12, and13 with the “benzyl chlorides”14, 15, 16, and subsequent retro-Claisen-reaction. The spiro compounds21a and39 were obtained byPPA-cyclisation of the keto acids35 and38, which in turn were prepared by aldol-reaction of the ketoness-hydrindacen-1-on and9a with phthalaldehydic acid to the olefinic keto acids33 and36 followed by catalytic hydrogenation.

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Literatur

  1. 15. Mitt.: Neudeck H. (1988) Monatsh. Chem.119: 625

    Google Scholar 

  2. Neudeck H. (1987) Monatsh. Chem.118: 627;

    Google Scholar 

  3. Neudeck H., Schlögl K., Tscheplak H. (1985) Monatsh. Chem.116: 789;

    Google Scholar 

  4. Neudeck H., Schlögl K., Tscheplak H. (1985) Monatsh. Chem.116: 661;

    Google Scholar 

  5. Neudeck H., Schlögl K. (1981) Monatsh. Chem.112: 801;

    Google Scholar 

  6. Neudeck H., Richter B., Schlögl K. (1979) Monatsh. Chem.110: 931;

    Google Scholar 

  7. Neudeck H., Schlögl K. (1979) Monatsh. Chem.110: 541;

    Google Scholar 

  8. Neudeck H., Schlögl K. (1977) Chem. Ber.110: 2624

    Google Scholar 

  9. Veröffentlichung in Vorbereitung

  10. Haslinger E., Neudeck H., Robien W. (1981) Monatsh. Chem.112: 405

    Google Scholar 

  11. Hofer O., Neudeck H. (1987) Monatsh. Chem.118: 1163

    Google Scholar 

  12. Neudeck H., Werner A. (in Vorbereitung)

  13. Patwardhan S. A. (1969) Indian J. Chem.7: 105

    Google Scholar 

  14. Isabelle M. E., Wightman R. H., Avdovich H. W., Laycock D. E. (1980) Can. J. Chem.58: 1344

    Google Scholar 

  15. Braun Jr. (1922) Berichte55: 1700;

    Google Scholar 

  16. I.G. Farbenind. (1929) D.R.P. 522271

  17. v. Braun, Gruber, Kirschbaum (1922) Berichte55: 3673

    Google Scholar 

  18. Granger R., Orzalesi H., Muratelle N. (1961) Compt. Rend.252: 1971

    Google Scholar 

  19. House H. O., Hudson Ch. B. (1970) J. Org. Chem.35: 647

    Google Scholar 

  20. Dynesen E. (1972) Acta Chem. Scand.26: 850

    Google Scholar 

  21. Duff D. A., Ingold C. K. (1934) J. Chem. Soc.: 87

  22. Treibs W., Mayer R., Madejski M. (1954) Chem. Ber.87: 356

    Google Scholar 

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  1. Institut für Organische Chemie, Universität Wien, A-1090, Wien, Österreich

    Horst K. Neudeck

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  1. Horst K. Neudeck
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Neudeck, H.K. Aromatische Spirane, 16. Mitt.: Darstellung von monound dianellierten 2,2′-Spirobiindan-1,1′-dionen. Monatsh Chem 120, 597–621 (1989). https://doi.org/10.1007/BF00810848

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  • DOI: https://doi.org/10.1007/BF00810848

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