Highly efficient cucurbit[8]uril-templated intramolecular photocycloaddition of 2-naphthalene-labeled poly(ethylene glycol) in aqueous solution

Journal of Organic Chemistry

Volumn 73, Issue 2, 2008, Pages 491-494

  Wu, Xiao Ling ^a   Luo, Lin ^a   Lei, Lei ^a   Liao, Gui Hong ^a   Wu, Li Zhu ^a   Tung, Chen Ho ^a  

^a UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION; IRRADIATION; METAL COMPLEXES; NAPHTHALENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

INTRAMOLECULAR PHOTOCYCLOADDITION;

POLYETHYLENE GLYCOLS;

DIMER; MACROCYCLIC COMPOUND; MACROGOL; NAPHTHALENE DERIVATIVE; WATER; BRIDGED COMPOUND; CUCURBIT(8)URIL; IMIDAZOLE DERIVATIVE; MACROGOL DERIVATIVE; NAPHTHALENE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL LABELING; COMPLEX FORMATION; CYCLOADDITION; DIMERIZATION; FLUORESCENCE; IRRADIATION; PHOTOREACTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; RADIATION EXPOSURE; SOLUTION AND SOLUBILITY; SPECTROFLUOROMETRY; ULTRAVIOLET RADIATION;

BRIDGED COMPOUNDS; CYCLIZATION; DIMERIZATION; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NAPHTHALENES; PHOTOCHEMISTRY; POLYETHYLENE GLYCOLS; SOLUTIONS; SPECTROMETRY, FLUORESCENCE; ULTRAVIOLET RAYS; WATER;

EID: 40949108379     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701998e     Document Type: Article

References (49)

1. (a) Jencks, W. P. Catalysis in Chemistry and Enzymology; McGraw-Hill: New York, 1969.
2. (b) Sanders, J. K. M. Chem. Eur. J. 1998, 4, 1378.
3. (c) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997.
4. (d) Svoboda, J.; König, B. Chem. Rev. 2006, 106, 5413.
5. (e) Huang, C. H.; Bassani, D. M. Eur. J. Org. Chem. 2005, 4041.
6. (a) Ramamurthy, V., Ed.; Photochemistry in Organized and Constrained Media; VCH: New York, 1991.
7. (b) Ramamurthy, V.; Schanze, K., Eds., Molecular and Supramolecular Photochemistry; Marcel Dekker: New York, 2001.
8. (c) Inoue, Y.; Ramamurthy, V., Eds.; Chiral Photochemistry; Marcel Dekker: New York, 2004.
9. (a) Weiss, R. G.; Ramamurthy, V.; Hammond, G. S. Acc. Chem. Res. 1993, 26, 530.
10. (b) Toda, F. Acc. Chem. Res. 1995, 28, 480.
11. (c) Turro, N. J. Acc. Chem. Res. 2000, 33, 637.
12. (d) Scheffer, J. R. Can. J. Chem. 2001, 79, 349.
13. (e) Sivaguru, J.; Natarajan, A.; Kaanumalle, L. S.; Shailaja, J.; Uppili, S.; Joy, A.; Ramamurthy, V. Acc. Chem. Res. 2003, 36, 509.
14. (f) Tung, C. H.; Wu, L.-Z.; Zhang, L. P.; Chen, B. Acc. Chem. Res. 2003, 36, 39.
15. (a) Inoue, Y. Chem. Rev. 1992, 92, 741.
16. (b) Takahashi, K. Chem. Rev. 1998, 98, 2013.
17. (c) Szejtli, J. Chem. Rev. 1998, 98, 1743.
18. (d) Bortolus, P.; Monti, S. In Photochemistry in Cyclodextrin Cavities: Advances in Photochemistry; Neckers, D. C., Volman, D. H., Bunau, G. V., Eds.; John Wiley: New York, 1996; pp 1-133.
19. (a) Bach, T.; Bergmann, H.; Grosch, B.; Harms, K. J. Am. Chem. Soc. 2002, 124, 7982.
20. (b) Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 966.
21. (c) Nakamura, A.; Inoue, Y. J. Am. Chem. Soc. 2005, 127, 5338.
22. (a) Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50.
23. (b) Harada, A.; Li, J.; Kamachi, M. Nature 1994, 370, 126.
24. (c) Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem., Int. Ed. 2004, 43, 6748.
25. (d) Yoshizawa, M.; Tamura, M.; Fujita, M. Science 2006, 312, 251.
26. (e) Nishioka, Y.; Yamaguchi, T.; Yoshizawa, M.; Fujita, M. J. Am. Chem. Soc. 2007, 129, 7000.
27. (f) Yoshizawa, M.; Takeyama, Y.; Kusukawa, T.; Fujita, M. Angew. Chem., Int. Ed. 2002, 41, 1347.
28. (g) Kaliappan, R.; Kaanumalle, L. S.; Natarajan, A.; Ramamurthy, V. Photochem. Photobiol. Sci. 2006, 5, 925.
29. (a) Mock, W. L. Top. Curr. Chem. 1995, 175, 1.
30. (b) Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Acc. Chem. Res. 2003, 36, 621.
31. (c) Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844.
32. (a) Jeon, W. S.; Ziganshina, A. Y.; Lee, J. W.; Ko, Y. H.; Kang, J.-K.; Lee, C.; Kim, K. Angew. Chem., Int. Ed. 2003, 42, 4097.
33. (b) Ko, Y. H.; Kim, K.; Kang, J. K.; Chun, H.; Lee, J. W.; Sakamoto, S.; Yamaguchi, K.; Fettinger, J. C.; Kim, K. J. Am. Chem. Soc. 2004, 126, 1932.
34. (c) Sindelar, V.; Silvi, S.; Kaifer, A. E. Chem. Commun. 2006, 2185.
35. (d) Sobransingh, D.; Kaifer, A. E. Org. Lett. 2006, 8, 3247.
36. (e) Feng, K.; Wu, L.-Z.; Zhang, L. P.; Tung, C. H. Dalton Trans. 2007, 3991.
37. (a) Jon, S. Y.; Ko, Y. H.; Park, S. H.; Kim, H.-J.; Kim, K. Chem. Commun. 2001, 1938.
38. (b) Lee, J. W.; Kim, K. P.; Choi, S. W.; Ko, Y. H.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Chem. Commun. 2002, 2692.
39. (a) Pattabiraman, M.; Natarajan, A.; Kaanumalle, L. S.; Ramamurthy, V. Org. Lett. 2005, 7, 529.
40. (b) Pattabiraman, M.; Natarajan, A.; Kaliappan, R.; Mague, J. T.; Ramamurthy, V. Chem. Commun. 2005, 4542.
41. (c) Pattabiraman, M.; Kaanumalle, L. S.; Natarajan, A.; Ramamurthy, V. Langmuir 2006, 22, 7605.
42. (a) Hammond, G. S.; Cole, R. S. J. Am. Chem. Soc. 1965, 87, 3256.
43. (b) Let, L.; Wu, L.-Z.; Wu, X. L.; Liao, G. H.; Luo, L.; Zhang, L. P.; Tung, C. H.; Ding, K. L. Tetrahedron Lett. 2006, 47, 4725 and references cited therein.
44. (c) Wu, X. L.; Lei, L.; Wu, L.-Z.; Liao, G. H.; Luo, L.; Shan, X. F.; Zhang, L. P.; Tung, C. H. Tetrahedron 2007, 63, 3133.
45. (a) Tung, C. H.; Wu, L.-Z.; Yuan, Z. Y.; Su, N. J. Am. Chem. Soc. 1998, 120, 11594.
46. (b) Tung, C. H.; Yuan, Z. Y.; Wu, L.-Z.; Weiss, R. G. J. Org. Chem. 1999, 64, 5156-5161.
47. (c) Tung, C. H.; Wu, L. Z. J. Chem. Soc., Faraday Trans. 1996, 92, 1381.
48. (d) Tung, C. H.; Li, Y.; Yang, Z. Q. J. Chem. Soc., Faraday Trans. 1994, 90, 947.
49. (e) Xu, M.; Wu, L.-Z.; Zhang, L. P.; Tung, C. H. Tetrahedron Lett. 2001, 42, 9249-9252.