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Darstellung und Kristallstrukturen halogenierter Carbonyl-derivate des Bicyclopentadienylidens

Preparation and crystal structures of halogenated carbonylic derivatives of bicyclopentadienylidene

  • Anorganische Und Physikalische Chemie
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Abstract

Treatment of dodecachlorobicyclopentenylidene1 with fuming nitric acid yields mainly octachlorobicyclopentenylidendione5 besides hexachloropentenylidentrione6. Both compounds are obtained as yellow crystalline solids. Octachlorobicyclopentadienylidene2 reacts with fuming nitric acid forming yellow α-halo-nitro-carbonyl-compounds7 and8. Thermical cleavage of NOCl from7 in nitrobenzene leads to the orange tetrachlorobicyclopentenylidentetraone9. The molecular structures of7 and8 are derived from their ir and mass spectra, whilst the molecular structure of5,6 and7 are established by single crystal x-ray diffraction. Bond distances and angles are given and discussed.

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Literatur

  1. Fenske D., Becher H. J., Chem. Ber.108, 2115 (1975).

    Google Scholar 

  2. Smith R. M., West R., J. Org. Chem.35, 2681 (1970).

    Google Scholar 

  3. Roedig A., Ziegler H., Chem. Ber.94, 1800 (1961).

    Google Scholar 

  4. McBee E. T., Ungnade H. G., Rakoff H., Dinbergs K., J. Amer. Chem. Soc.77, 4379 (1955).

    Google Scholar 

  5. Claus A., Mielcke P., Ber. dtsch. chem. Ges.19, 1184 (1886).

    Google Scholar 

  6. Ciamician G., Silber P., Ber. dtsch. chem. Ges.20, 698, 2594 (1887);Angeli A., Ciamician G., ebenda24, 74 (1891).

    Google Scholar 

  7. Mark V., Tetrahedron Lett.1961, 333.

  8. Brown J. F., J. Amer. Chem. Soc.77, 6341 (1955).

    Google Scholar 

  9. Ammon H. L., Wheeler G. L., Tetrahedron29, 2695 (1973).

    Google Scholar 

  10. Structural Reports38 b, 1068 (1972).

  11. Barss W. M., J. Chem. Phys.27, 1260 (1957).

    Google Scholar 

  12. Karle J. L., Karle J., J. Chem. Phys.36, 1969 (1962).

    Google Scholar 

  13. Piutti A.,Mazza F. P., Chem. Zentralbl.1927, 240.

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Niessing, J., Fenske, D. Darstellung und Kristallstrukturen halogenierter Carbonyl-derivate des Bicyclopentadienylidens. Monatsh Chem 113, 1225–1238 (1982). https://doi.org/10.1007/BF00808737

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  • DOI: https://doi.org/10.1007/BF00808737

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