Supramolecular organization based on van der Waals forces: Syntheses and solid state structures of isomeric [6.6] cyclophanes with 2,5-diselenahex-3-yne bridges

European Journal of Organic Chemistry

Volumn , Issue 14, 2009, Pages 2267-2274

  Lari, Alberth ^a   Gleiter, Rolf ^a   Rominger, Frank ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkynes; Cyclophanes; Diselenaalkynes; Selenium; Supramolecular chemistry; van der Waals contacts

Indexed keywords

EID: 66149116726     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900106     Document Type: Article

References (35)

1. a) J. W. Steed, J. L. Atwood, Supramolecular Chemistry, John Wiley & Sons, Chichester 2000;
2. b) H. J. Schneider, A. Yatsimir- sky, Principles and Methods in Supramolecular Chemistry, John Wiley & Sons, Chichester, 2000.
3. a) J. M. Lehn, Supramolecular Chemistry: Concepts and Perspectives VCH, Weinheim, 1995
4. b)F. Vogtle, Supramolekulare Chemie, Teubner, Stuttgart, 1992;
5. c) D. Philip, J. F. Stoddart, Angew. Chem. 1996, 108, 1243-1286; Angew. Chem. Int. Ed. Engl. 1996, 55, 1155-1196.
6. D. T. Bong, T. D. Clark, J. R. Granja, M. R. Ghadiri, Angew. Chem. 2001, 113, 1016 -1041; Angew. Chem. Int. Ed. 2001, 40, 988-1101.
7. W. Saenger, in: Inclusion Compounds, vol. 2 (Eds.:J. L. Atwood, J. E. Davies, D. D. McNicol), Academic Press, London, 1984, p. 231-259.
8. D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591-593.
9. a) D. B. Werz, T. H. Staeb, C. Benisch, B. J. Rausch, F. Rominger, R. Gleiter, Org. Lett. 2002, 4, 339-342;
10. b) D. B. Werz, R. Gleiter, F. Rominger, J. Am. Chem. Soc. 2002, 124, 10638-10639;
11. c) R. Gleiter, D. B. Werz, B.J. Rausch, Chem. Eur. J. 2003, 9, 2676-2683;
12. d) D. B. Werz, B. J. Rausch, R. Gleiter, Tetrahedron Lett. 2002, 43, 5767-5769;
13. e) J. H. Schulte, D. B. Werz, F. Rominger, R. Gleiter, Org. Biomol. Chem. 2003, 1, 2788-2794;
14. f) D. B. Werz, R. Gleiter, F. Rominger, Organometallics 2003, 22, 843-849.
15. a) D. B. Werz, R. Gleiter, F. Rominger, J. Org. Chem. 2002, 67, 4290-4297;
16. b) D. B. Werz, R. Gleiter, J. Org. Chem. 2003, 68, 9400-9405;
17. c) R. Gleiter, D. B. Werz, Chem. Lett. 2005, 34, 126-131;
18. d) D. B. Werz, F. R. Fischer, S. C. Kornmayer, F. Rominger, R. Gleiter, J. Org. Chem. 2008, 73, 8021 -8029.
19. a) C. Bleiholder, D. B. Werz, H. Koppel, R. Gleiter, J. Am. Chem. Soc. 2006, 128, 2666-2674;
20. b) C. Bleiholder, R. Gleiter, D. B. Werz, H. Koppel, Inorg. Chem. 2007, 46, 2249-2260.
21. a) T. Wirth, Angew. Chem. 2000, 112, 3891-3900; Angew. Chem. Int. Ed. 2000, 39, 3740-3749;
22. b) M. Tiecco, Top. Curr. Chem. 2000, 208,7-54;
23. c) M. Iwaoka, S. Tomoda, Top. Curr. Chem. 2000, 208,55-80.
24. a) C. Benisch, S. Bethke, R. Gleiter, T. Oeser, H. Pritzkow, F. Rominger, Eur. J. Org. Chem. 2000, 2479-2488;
25. b) L. Brandsma, Preparative Acetylene Chemistry, 2nd ed., Elsevier, Amsterdam, 988.
26. M. Hojjatie, S. Muralidharan, H. Freiser, Tetrahedron 1989, 45, 1611-1622.
27. A. Lari, F. Rominger, R. Gleiter, Rev. Roum. Chim. 2006, 51, 851-854.
28. a) A. Bondi, J. Phys. Chem. 1964, 68, 441-451;
29. rd ed., Cornell University Press, Ithaca, New York, 1973.
30. a) T. Steiner, Angew. Chem. 2002, 114,50-80; Angew. Chem. Int. Ed. 2002, 41,48-78;
31. b) G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond: Applications to Structural Chemistry and Biology, Oxford Univ. Press, 1999.
32. M. Nishio, M. Hirota, Y. Umezawa, CH/n Interaction: Evidence, Nature and Consequences, Wiley-VCH, New York, 1998.
33. M. Srinivasan, S. Sankararaman, H. Hopf, I. Dix, P. G. Jones, J. Org. Chem. 2001, 66, 4299-4303.
34. G. M. Sheldrick, SADABS V2.03, Bruker Analytical X-ray-Division, Madison, Wisconsin, 2001.
35. G. M. Sheldrick, SHELXTL V5.10, Bruker Analytical X-ray- Division, Madison, Wisconsin, 1997.