A highly efficient approach to [4]pseudocatenanes by threefold metathesis reactions of a triptycene-based tris[2]pseudorotaxane

Journal of the American Chemical Society

Volumn 127, Issue 38, 2005, Pages 13158-13159

  Zhu, Xiao Zhang ^a   Chen, Chuan Feng ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATENANE; PSEUDOCATENANE DERIVATIVE; PSEUDOROTAXANE; ROTAXANE; TRIPTYCENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; MOLECULAR MODEL; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY;

CATENANES; CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ROTAXANES;

EID: 25444436478     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0546020     Document Type: Article

References (29)

1. (a) Molecular Catenanes, Rotaxanes and Knots; Sauvage, J.-P., Dietrich-Buchecker, C., Eds.; Wiley-VCH: Weinheim, Germany, 1999.
2. (b) Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 1643-1663.
3. (c) Breault, G. A.; Hunter, C. A.; Meyers, P. C. Tetrahedron 1999, 55, 5265-5293.
4. (a) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348-3391.
5. (b) Collin, J.-P.; Dietrich-Buchecker, C.; Gaviòa, P.; Jimenez-Molero, M. C.; Sauvage, J.-P. Acc. Chem. Res. 2001, 34, 477-487.
6. Schalley, C. A.; Beizai, K.; Vögtle, F. Acc. Chem. Res. 2001, 34, 465-476.
7. (d) Leigh, D. A.; Wong, J. K. Y.; Dehez, F.; Zerbetto, F. Science 2003, 424, 174-179.
8. (e) Badjiæ, J. D.; Balzani, V.; Credi, A.; Silvi, S.; Stoddart, J. F. Science 2004, 303, 1845-1849.
9. Some recent examples: (a) Chichak, K. S.; Cantrill, S. J.; Pease, A. R.; Chiu, S.; Cave, G. W. V.; Atwood, J. L.; Stoddart, J. F. Science 2004, 304, 1308-1311.
10. (b) Wang, L.; Vysotsky, M. O.; Bogdan, A.; Bolte, M.; Böhmer, V. Science 2004, 304, 1312-1314.
11. (c) Ko, Y. H.; Kim, K.; Kang, J.; Chun, H.; Lee, J. W.; Sakamoto, S.; Yamaguchi, K.; Fettinger, J. C.; Kim, K. J. Am. Chem. Soc. 2004, 126, 1932-1933.
12. (d) Liu, Y.; Bonvallet, P. A.; Vignon, S. A.; Khan, S. I.; Stoddart, J. F. Angew. Chem., Int. Ed. 2005, 44, 3050-3055.
13. (e) Sambrook, M. R.; Beer, P. D.; Wisner, J. A.; Paul, R. L.; Cowley, A. R. J. Am. Chem. Soc. 2004, 126, 15364-15365.
14. (a) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.
15. (b) Kelly, T. R. Acc. Chem. Res. 2001, 34, 514-522.
16. (c) Yang, J. S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 11864-11873.
17. (d) Godinez, C. E.; Zepeda, G.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2002, 124, 4701-4707.
18. (e) Zhu, X. Z.; Chen, C. F. J. Org. Chem. 2005, 70, 917-924.
19. Ashton, P. R.; Campbell, P. J.; Chrystal, E. J. T.; Glink, P. T.; Menzer, S.; Philip, D.; Spencer, N.; Stoddart, J. F.; Tasker, P. A.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1869-1871.
20. (a) Li, Z. T.; Stein, P. C.; Svenstrup, N.; Lund, K. H.; Becher, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2524-2528.
21. (b) Li, Z. T.; Becher, J. Chem. Commun. 1996, 639-640.
22. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
23. Chung, Y.; Duerr, B. F.; Mckelvey, T. A.; Nanjappan, P.; Czarnik, A. W. J. Org. Chem. 1989, 54, 1018-1032.
24. Ashton, P. R.; Bartsch, R. A.; Cantrill, S. J.; Hanes, R. E., Jr.; Hickingbottom, S. K.; Lowe, J. N.; Preece, J. A.; Stoddart, J. F.; Talanov, V. S.; Wang, Z. H. Tetrahedron Lett. 1999, 40, 3661-3664.
25. 6 (Supporting Information).
26. -1, which suggests that 1 binds to dialkylammonium ions with a similar strength as does DB24C8 (Supporting Information).
27. Similar procedure to obtain pseudorotaxanes has been used by Stoddart et al.; Ashton, P. R.; Baxter, I.; Tyfe, M. C. T.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 2297-2307.
28. 3)(IMes)Ru=CHPh, [IMes = 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]: Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
29. 2Ru=CHPh] was used, we found the product was obtained in a low yield (∼30%) even with a large amount of the ruthenium catalyst (40-60 mol %) within a long reaction time. Moreover, the byproducts and the residual ruthenium were very difficult to remove.