Self-sorting under solvent-free conditions: One-pot synthesis of a hetero[3]rotaxane

Organic Letters

Volumn 13, Issue 17, 2011, Pages 4660-4663

  Chen, Pei Nung ^a   Lai, Chien Chen ^b,c   Chiu, Sheng Hsien ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

^c CHINA MEDICAL UNIVERSITY HOSPITAL   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ROTAXANE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

MOLECULAR STRUCTURE; ROTAXANES; STEREOISOMERISM;

EID: 80052209690     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201870h     Document Type: Article

References (25)

1. Molecular Electronics: Science and Technology; Aviram, A., Ratner, M., Eds.; New York Academy of Sciences: New York, 1998.
2. Collier, C. P.; Mattersteig, G.; Wong, E. W.; Luo, Y.; Beverly, K.; Sampaio, J.; Raymo, F. M.; Stoddart, J. F.; Heath, J. R. Science 2000, 289, 1172
3. Saha, S.; Leung, K. C.-F.; Nguyen, T. D.; Stoddart, J. F.; Zink, J. I. Adv. Funct. Mater. 2007, 17, 685
4. Green, J. E.; Choi, J. W.; Boukai, A.; Bunimovich, Y.; Johnston-Halperin, E.; DeIonno, E.; Luo, Y.; Sheriff, B. A.; Xu, K.; Shin, Y. S.; Tseng, H.-R.; Stoddart, J. F.; Heath, J. R. Nature 2007, 445, 414
5. Lehn, J.-M. Science 2002, 295, 2400
6. Wu, A. X.; Isaacs, L. J. Am. Chem. Soc. 2003, 125, 4831
7. Mukhopadhyay, P.; Wu, A. X.; Isaacs, L. J. Org. Chem. 2004, 69, 6157
8. Jiang, W.; Winkler, H. D. F.; Schalley, C. A. J. Am. Chem. Soc. 2008, 130, 13852
9. Jiang, W.; Schaefer, A.; Mohr, P. C.; Schalley, C. A. J. Am. Chem. Soc. 2010, 132, 2309
10. Collin, J.-P.; Durola, F.; Heitz, V.; Reviriego, F.; Sauvage, J.-P.; Trolez, Y. Angew. Chem., Int. Ed. 2010, 49, 10172
11. Busseron, E.; Romuald, C.; Coutrot, F. Chem.-Eur. J. 2010, 16, 10062
12. Hsueh, S.-Y.; Kuo, C.-T.; Lu, T.-W.; Lai, C.-C.; Liu, Y.-H.; Hsu, H.-F.; Peng, S.-M.; Chen, C.-h.; Chiu, S.-H. Angew. Chem., Int. Ed. 2010, 49, 9170
13. Strutt, N. L.; Forgan, R. S.; Spruell, J. M.; Botros, Y. Y.; Stoddart, J. F. J. Am. Chem. Soc. 2011, 133, 5668
14. Yoshii, T.; Kohsaka, Y.; Moriyama, T.; Suzuki, T.; Koyama, Y.; Takata, T. Supramol. Chem. 2011, 23, 65
15. Leontiev, A. V.; Jemmett, C. A.; Beer, P. D. Chem.-Eur. J. 2011, 17, 816
16. Trost, B. M. Science 1991, 254, 1471
17. Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025
18. Solvent-Free Organic Synthesis; Tanaka, K., Ed.; Wiley-VCH: Weinheim, 2004.
19. A similar method has been used to generate pseudorotaxanes as solids for the efficient syntheses of [2]- and [4]rotaxanes; see: Hsueh, S.-Y.; Cheng, K.-W.; Lai, C.-C.; Chiu, S.-H. Angew. Chem., Int. Ed. 2008, 47, 4436
20. Händel, M.; Plevoets, M.; Gestermann, S.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 1199
21. Hsu, C.-C.; Chen, N.-C.; Lai, C.-C.; Liu, Y.-H.; Peng, S.-M.; Chiu, S.-H. Angew. Chem., Int. Ed. 2008, 47, 7475
22. Hsu, C.-C.; Lai, C.-C.; Chiu, S.-H. Tetrahedron 2009, 65, 2824
23. Boger, D. L. Chem. Rev. 1986, 86, 781
24. Hamasaki, A.; Ducray, R.; Boger, D. L. J. Org. Chem. 2006, 71, 185
25. Blackman, M. L.; Royzen, M.; Fox, J. M. J. Am. Chem. Soc. 2008, 130, 13518