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Synthese von Propellanen aus 1,8-Dihydroxynaphthalin: 3,7,11,15-Tetraoxa[4,5,6-12,13,14-dinaphtho(1′,8′)]-(7.7.1)propellan

Use of 1,8-dihydroxynaphthalene for the synthesis of propellanes. 3,7,11,15-tetraoxa[4,5,6-12,13,14-dinaphtho(1′,8′)]-(7.7.1)propellane

4. Mitt. über Propellane

  • Organische Chemie und Biochemie
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Abstract

Condensation of 1,1,2,2,-tetrabromomethylcyclopropane with 1,8-dihydroxynaphthalene yielded the (7.7.1)-type propellane. The “peri effect” on the reaction and the product conformation is discussed. As a result condensation of 1,1-dibromomethylcyclopropane withperi-dihydroxynaphthalene gives the diether-type compound2 instead of the expected spirane2′.

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Literatur

  1. Stohrer, W. D., Hoffman, R., J. Amer. Chem. Soc.94, 779 (1972).

    Google Scholar 

  2. Herr, M. L., Tetrahedron33, 1897 (1977).

    Google Scholar 

  3. Buchta, E., Kröniger, A., Chimia23, 225 (1969).

    Google Scholar 

  4. Wiberg, K. B., Bailey, W. F., Jason, M. E., J. Org. Chem.41, 2711 (1976).

    Google Scholar 

  5. Jason, M. E., McGinnety, J. A., Wiberg, K. B. J. Amer. Chem. Soc.96, 6531 (1974).

    Google Scholar 

  6. Warner, P., La Rose, R., Schleis, T., Tetrahedron Lett.1974, 1409.

  7. Weinges, K., Klessing, K., Kolb, R., Chem Ber.106, 2298 (1973).

    Google Scholar 

  8. Rowe, J. W., Melera, A., Arigoni, D., Jeger, O., Ruzicka, L., Helv. Chim. Acta40, 1 (1957).

    Google Scholar 

  9. Dauben, W. G., Laug, P., Tetrahedron Lett.1962, 453.

  10. Vogel, E., Königshofer, H., Müllen, K., Oth, J. F. M., Angew. Chem.86, 229 (1974).

    Google Scholar 

  11. Jamrozik, J., J. für prakt. Chemie321, 437 (1979).

    Google Scholar 

  12. Jamrozik, J., Mh. Chem.111, 643 (1980).

    Google Scholar 

  13. Smoliński, S., Jamrozik, J., Tetrahedron27, 4977 (1971).

    Google Scholar 

  14. Smoliński, S., Jamrozik, J., Tetrahedron31, 1237 (1975).

    Google Scholar 

  15. Smoliński, S., Jamrozik, J., Jamrozik, M., Mh. Chem.108 1145 (1977).

    Google Scholar 

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Authors and Affiliations

  1. Institut für Chemie, Jagellonische Universität, PL-30-060, Kraków, Polen

    Janusz Jamrozik

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  1. Janusz Jamrozik
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Jamrozik, J., Propellanes III. J. für prakt. Chemie, im Druck (1980).

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Jamrozik, J. Synthese von Propellanen aus 1,8-Dihydroxynaphthalin: 3,7,11,15-Tetraoxa[4,5,6-12,13,14-dinaphtho(1′,8′)]-(7.7.1)propellan. Monatshefte für Chemie 112, 785–790 (1981). https://doi.org/10.1007/BF00899781

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  • DOI: https://doi.org/10.1007/BF00899781

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