Temporary and permanent trapping of the metastable twisted conformer of an overcrowded chromic alkene via encapsulation

Journal of the American Chemical Society

Volumn 134, Issue 42, 2012, Pages 17420-17423

  Takezawa, Hiroki ^a   Murase, Takashi ^a   Fujita, Makoto ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COLOR CHANGES; COORDINATION CAGE; IN-SITU; SELF-ASSEMBLED; TWISTED CONFORMATION;

CHEMISTRY; SYNTHESIS (CHEMICAL);

OLEFINS;

ALKENE; CHROMIC ALKENE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL STRUCTURE; COLOR; ENCAPSULATION;

EID: 84867749104     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja308101a     Document Type: Article

References (37)

1. Overcrowded alkenes have been studied for over a century since bifluorenylidene was first synthesized: de la Harpe, C.; van Dorp, W. E. Ber. Dtsch. Chem. Ges. 1875, 8, 1048
2. Sandstörm, J. In The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; The Chemistry of Functional Groups, Supplement A3; Wiley: New York, 1997; p 1253.
3. Day, J. H. Chem. Rev. 1963, 63, 65
4. Bercovici, T.; Korenstein, R.; Muszkat, K. A.; Fischer, E. Pure Appl. Chem. 1970, 24, 531
5. Fischer, E. Rev. Chem. Intermed. 1984, 5, 393
6. Fanselow, D. L.; Drickamer, H. G. J. Chem. Phys. 1974, 61, 4567
7. Evans, D. H.; Xie, N. J. Am. Chem. Soc. 1983, 105, 315
8. Beck, A.; Gompper, R.; Polborn, K.; Wagner, H.-U. Angew. Chem., Int. Ed. Engl. 1993, 32, 1352
9. Browne, W. R.; Pollard, M. M.; de Lange, B.; Meetsma, A.; Feringa, B. L. J. Am. Chem. Soc. 2006, 128, 12412
10. Luo, J.; Song, K.; Gu, F.; Miao, Q. Chem. Sci. 2011, 2, 2029
11. Shoham, G.; Cohen, S.; Suissa, R. M.; Agnarat, I. In Molecular Structure: Chemical Reactivity and Biological Activity; Stezowski, J. J.; Huang, J.-L.; Shao, M. C., Eds.; Oxford University Press: Oxford, U.K., 1998; p 290.
12. Biedermann, P. U.; Stezowski, J. J.; Agranat, I. In Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Stamford, CT, 1998; Vol. 4, p 245.
13. Biedermann, P. U.; Stezowski, J. J.; Agranat, I. Eur. J. Org. Chem. 2001, 15
14. Levy, A.; Biedermann, U.; Agranat, I. Org. Lett. 2000, 2, 1811
15. Biedermann, P. U.; Stezowski, J. J.; Agranat, I. Chem. Commun. 2001, 954
16. Levy, A.; Pogodin, S.; Cohen, S.; Agranat, I. Eur. J. Org. Chem. 2007, 5198
17. Suzuki, T.; Fukushima, T.; Miyashi, T.; Tsuji, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2495
18. Biedermann, P. U.; Stezowski, J. J.; Agranat, I. Chem.-Eur. J. 2006, 12, 3345
19. Schönberg, A.; Mustafa, A.; Sobhy, M. E. E.-D. J. Am. Chem. Soc. 1953, 75, 3377
20. Ballester, M.; Castaer, J.; Riera, J.; de la Fuente, G.; Camps, M. J. Org. Chem. 1985, 50, 2287
21. Feringa, B. L.; Jager, W. F.; de Lange, B. Tetrahedron Lett. 1992, 33, 2887
22. Levy, A.; Biedermann, P. U.; Cohen, S.; Agranat, I. J. Chem. Soc., Perkin Trans. 2 2001, 2329
23. Molins, E.; Miravitlles, C.; Espinosa, E.; Ballester, M. J. Org. Chem. 2002, 67, 7175
24. Levy, A.; Cohen, S.; Agranat, I. Org. Biomol. Chem. 2003, 1, 2755
25. Haneda, T.; Kawano, M.; Fujita, M. Angew. Chem., Int. Ed. 2007, 46, 6643
26. Horiuchi, S.; Murase, T.; Fujita, M. J. Am. Chem. Soc. 2011, 133, 12445
27. Ams, M. R.; Ajami, D.; Craig, S. L.; Yang, J.-S.; Rebek, J., Jr. J. Am. Chem. Soc. 2009, 131, 13190
28. Ams, M. R.; Ajami, D.; Craig, L.; Yang, J.-S.; Rebek, J., Jr. Beilstein J. Org. Chem. 2009, 5, 79
29. Tzeli, D.; Theodorakopoulos, G.; Petsalakis, I. D.; Ajami, D.; Rebek, J., Jr. J. Am. Chem. Soc. 2012, 134, 4346
30. Yanai, N.; Kitayama, K.; Hijikata, Y.; Sato, H.; Matsuda, R.; Kubota, Y.; Takata, M.; Mizuno, M.; Uemura, T.; Kitagawa, S. Nat. Mater. 2011, 10, 787
31. Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 2002, 124, 13576
32. Yoshizawa, M.; Sato, N.; Fujita, M. Chem. Lett. 2005, 34, 1392
33. Furusawa, T.; Kawano, M.; Fujita, M. Angew. Chem., Int. Ed. 2007, 46, 5717
34. Klosterman, J. K.; Iwamura, M.; Tahara, T.; Fujita, M. J. Am. Chem. Soc. 2009, 131, 9478
35. Symmetry analysis of the host cage can be used to elucidate the symmetry of an encapsulated guest. See: Kusukawa, T.; Yoshizawa, M.; Fujita, M. Angew. Chem., Int. Ed. 2001, 40, 1879
36. Hanzlik, R. P. Org. Synth. 1977, 56, 112
37. Berger, J. J. Prakt. Chem. 1991, 333, 677