Synthesis of polyyne rotaxanes

Organic Letters

Volumn 14, Issue 13, 2012, Pages 3424-3426

  Movsisyan, Levon D ^a   Kondratuk, Dmitry V ^a   Franz, Michael ^b   Thompson, Amber L ^a   Tykwinski, Rik R ^b   Anderson, Harry L ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

POLYACETYLENE DERIVATIVE; ROTAXANE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYACETYLENES; ROTAXANES;

EID: 84863611838     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301392t     Document Type: Article

References (31)

1. Diederich, F. Nature 1994, 369, 199-207
2. Szafert, S; Gladysz, J. A. Chem. Rev. 2006, 106, PR1-PR33
3. Chalifoux, W. A.; Tykwinski, R. R. C. R. Chim. 2009, 12, 341-358
4. Eastmond, R.; Johnson, T. R.; Walton, D. R. M. Tetrahedron 1972, 28, 4601-4616
5. Zheng, Q.; Bohling, J. C.; Peters, T. B.; Frisch, A. C.; Hampel, F.; Gladysz, J. A. Chem.-Eur. J. 2006, 12, 6486-6505
6. Gibtner, T.; Hampel, F.; Gisselbrecht, J.-P.; Hirsch, A. Chem.-Eur. J. 2002, 8, 408-432
7. Chalifoux, W. A.; Tykwinski, R. R. Nat. Chem. 2010, 2, 967-971
8. Eisler, S.; Slepkov, A. D.; Elliott, E.; Luu, T.; McDonald, R.; Hegmann, F. A.; Tykwinski, R. R. J. Am. Chem. Soc. 2005, 127, 2666-2676
9. Wang, C.; Batsanov, A. S.; Bryce, M. R.; Martín, S.; Nichols, R. J.; Higgins, S. J.; García-Suárez, V. M.; Lambert, C. J. J. Am. Chem. Soc. 2009, 131, 15647-15654
10. Stahl, J.; Bohling, J. C.; Bauer, E. B.; Peters, T. B.; Mohr, W.; Martín-Alvarez, J. M.; Hampel, F.; Gladysz, J. A. Angew. Chem., Int. Ed. 2002, 41, 1871-1876
11. de Quadras, L.; Bauer, E. B.; Mohr, W.; Bohling, J. C.; Peters, T. B.; Martín-Alvarez, J. M.; Hampel, F.; Gladysz, J. A. J. Am. Chem. Soc. 2007, 129, 8296-8309
12. Taylor, T. J.; Gabbaï, F. P. Organometallics 2006, 25, 2143-2147
13. Zhao, C.; Kitaura, R.; Hara, H.; Irle, S.; Shinohara, H. J. Phys. Chem. C 2011, 115, 13166-13170
14. Huuskonen, J.; Buston, J. E. H.; Scotchmer, N. D.; Anderson, H. L. New J. Chem. 1999, 23, 1245-1252
15. Simpkins, S. M. E.; Kariuki, B. M.; Cox, L. R. J. Organomet. Chem. 2006, 691, 5517-5523
16. Sugiyama, J.; Tomita, I. Eur. J. Org. Chem. 2007, 4651-4653
17. Shir, I. B.; Sasmal, S.; Mejuch, T.; Sinha, M. K.; Kapon, M.; Keinan, E. J. Org. Chem. 2008, 73, 8772-8779
18. Langton, M. J.; Matichak, J. D.; Thompson, A. L.; Anderson, H. L. Chem. Sci. 2011, 2, 1897-1901
19. Frampton, M. J.; Anderson, H. L. Angew. Chem., Int. Ed. 2007, 46, 1028-1064
20. While this manuscript was in preparation we became aware of similar work, carried out in parallel, on a C8 rotaxane of macrocycle 3 with organometallic end groups: Weisbach, N.; Baranová, Z.; Gauthier, S.; Reibenspies, J. H.; Gladysz, J. A. Chem. Commun. 2012, 48, DOI: 10.1039/c2cc33321j. A cyclodextrin-based C12 rotaxane was reported by Sugiyama and Tomita but not fully characterized (ref 11c).
21. Sato, Y.; Yamasaki, R.; Saito, S. Angew. Chem., Int. Ed. 2009, 48, 504-507
22. Berná, J.; Crowley, J. D.; Goldup, S. M.; Hänni, K. D.; Lee, A.-L.; Leigh, D. A. Angew. Chem., Int. Ed. 2007, 46, 5709-5713
23. Crowley, J. D.; Goldup, S. M.; Gowans, N. D.; Leigh, D. A.; Ronaldson, V. E.; Slawin, A. M. Z. J. Am. Chem. Soc. 2010, 132, 6243-6248
24. Cosier, J.;; Glazer, A. M. J. Appl. Crystallogr. 1986, 19, 105-107
25. Nowell, H.; Barnett, S. A.;; Christensen, K. E.; Teat, S. J.;; Allan, D. R. J. Synchrotron Rad. 2012, 19, 435-441).
26. (Palatinus, L.;; Chapuis, G. J. Appl. Crystallogr. 2007, 40, 786-790
27. (Betteridge, P. W.; Carruthers, J. R.; Cooper, R. I.;; Prout, K.; Watkin, D. J. J. Appl. Crystallogr. 2003, 36, 1487
28. (Cooper, R. I.;; Thompson, A. L.; Watkin, D. J. J. Appl. Crystallogr. 2010, 43, 1100-1107
29. 3. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre (CCDC 885635), and copies of these data can be obtained free of charge via www.ccdc.cam.ac.uk/ data-request/cif.
30. Pu, Y.-J.; Harding, R. E.; Stevenson, S. G.; Namdas, E. B.; Tedeschi, C.; Markham, J. P. J.; Rummings, R. J.; Burn, P. L.; Samuel, I. D. W. J. Mater. Chem. 2007, 17, 4255-4264
31. Sacksteder, L. A.; Lee, M.; Demas, J. N.; DeGraff, B. A. J. Am. Chem. Soc. 1993, 115, 8230-8238