Warianty tytułu
Języki publikacji
Abstrakty
The syntheses of two new centrohexaindane derivatives bearing methyl groups in their molecular propellane-type cavities are described. These new topologically non-planar hydrocarbons, 1,8-dimethylcentrohexaindane 6 and 1,4,8,28-tetramethylcentrohexaindane 7 were obtained from suitable 1,3-indanediones following the shortest aufbau strategy, the propellane route, representing a six-step access to these unusually highly condensed polycyclic hydrocarbons. X-ray single crystal structure analysis of 6 revealed that the presence of the two methyl groups in the cavities of the centrohexaindane framework does not give rise to significant distortion of the Td-symmetrical molecular skeleton; however, their efficient hiding within two of the four equivalent cavities allows for strong intermolecular disorder in the crystal.
Czasopismo
Rocznik
Tom
Strony
875-892
Opis fizyczny
Bibliogr. 33 poz., rys.
Twórcy
autor
autor
autor
autor
- Department of Chemistry, Bielefeld University, Universitätsstraße 25, D-33615 Bielefeld, Germany, dietmar.kuck@uni-bielefeld.de
Bibliografia
- l. Kuck D. and Schuster A., Angew. Chem., 100, 1222 (1988); Angew. Chem., Int. Ed. Engl., 27, 1192 (1988).
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- 3. Harary F., in Balaban A.T. (Ed.), Chemical Applications ofGraph Theory, Academic Press, London, pp. 5-9(1976).
- 4. Simon J., in King R.B. and Rouvray D.H. (Eds.), Graph Theory and Topology in Chemistry, Elsevier, Amsterdam, pp. 43-75 (1987).
- 5. Kuck D., Pure Appl. Chem., 78, 749 (2006).
- 6. Kuck D., Chem. Rev., 106, 4885 (2006).
- 7. Kuratowski C., Fund. Math., 15, 271 (1930).
- 8. Lipkowitz K., Larter R.M. and Boyd D.B., J. Am. Chem. Soc., 102, 85 (1980).
- 9. (a) Paquette L.A. and Vazeux M., Tetrahedron Lett., 22, 291 (1981); (b) Paquette L.A., Williams R.V.,Vazeux M. and Browne A.R., J. Org. Chem., 49, 2194 (1984).
- 10. (a) Paquette L.A., Top. Curr. Chem., 79,41 (1979); (b) Paquette L.A., Top. Curr. Chem., 119, l (1984);(c) Paquette L.A. and Doherty A.M., Polyquinane Chemistry, Synthesis and Reactions; Springer-Yerlag,Berlin, (l987).
- 11. Kuck D., Paisdor B. and Grutzmacher H.F., Chem. Ber., 120, 589 (1987).
- 12. Paisdor B., Grutzmacher H.F. and Kuck D., Chem. Ber., 121, 1307 (1988).
- 13. Harig M. and Kuck D., Eur. J. Org. Chem., 1647 (2006).
- 14. Tellenbróker J., Barth D., Neumann B., Stammler H.G. and Kuck D., Org. Biomol. Chem., 3,570 (2005).
- 15. Kuck D., Paisdor B. and Gestmann D., Angew. Chem., 106, 1326 (1994); Angew. Chem., Int. Ed. Engl., 33,1251(1994).
- 16. Kuck D., Synlett, 949 (1996).
- 17. Kuck D., Top. Curr. Chem., 196, 167 (1998).
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- 19. Kuck D., Krause R.A., Gestmann D., Posteher F. and Schuster A., Tetrahedron, 54, 5247 (1998).
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- 22. Paisdor B. and Kuck D., J. Org. Chem., 56, 4753 (1991).
- 23. CCDC 622544 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data.request/cif.
- 24. Kuck D., Tellenbröker J., Bögge H., Strube J., Neumann B. and Stammler H.G., Unpublished results.
- 25. Buckle D.R., Morgan NJ. and Ross J.W., J. Med. Chem., 16, 1334 (1973).
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- 27. Diels O. and Alder K., Chem. Ber., 62, 544 (1929).
- 28. Kuck D., Org. Mass Spectrom., 29, 113 (1994).
- 29. Bloch R. and Orvane P., Synth. Commun., 11, 913 (1981).
- 30. Yamawaki J. and Ando T., Chem. Lett., 755 (1979).
- 31. Kuck D., Angew. Chem., 96, 515 (1984); Angew. Chem., Int. Ed. Engl., 23, 508 (1984).
- 32. Kuck D., Chem. Ber., 127, 409 (1994).
- 33. Radziszewski B. and Wispek P., Ber. Deutsch. Chem. Ges., 15, 1747 (1882).
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ5-0014-0048