A new, aqueous 1H NMR shift reagent based on host-guest molecular recognition principles for organic compound structural analysis: Non-covalent π-π and hydrophobic interactions using a supramolecular host, [Cp*Rh(2′-deoxyadenosine)]3(OTf)3

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7151-7156

  Ogo, Seiji ^a,b   Nakamura, Shigeyuki ^c   Chen, Hong ^a   Isobe, Kiyoshi ^c   Watanabe, Yoshihito ^b   Fish, Richard H ^a  

^a LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^c Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000892874     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972204c     Document Type: Article

References (38)

1. (a) Elgavish, G. A.; Reuben, J. J. Am. Chem. Soc. 1976, 98, 4755.
2. (b) Reuben, J. J. Am. Chem. Soc. 1976, 98, 3726.
3. (c) Elgavish, G. A.; Reuben, J. J. Am. Chem. Soc. 1977, 99, 1762.
4. (d) Reuben, J. J. Am. Chem. Soc. 1977, 99, 1765.
5. (e) Elgavish, G. A.; Reuben, J. J. Am. Chem. Soc. 1977, 99, 5590.
6. (f) Elgavish, G. A.; Reuben, J. J. Am. Chem. Soc. 1978, 100, 3617.
7. (g) Reuben, J. J. Am. Chem. Soc. 1980, 102, 2232.
8. Horrocks, W. DeW., Jr; Hove, E. G. J. Am. Chem. Soc. 1978, 100, 4386.
9. (a) Peters, J. A.; Vijverberg, C. A. M.; Kieboom, A. P. G.; Bekkum, H. Tetrahedron Lett. 1983, 24, 3141.
10. (b) Kabuto, K.; Sasaki, Y. J. Chem. Soc., Chem. Commun. 1984, 316.
11. (c) Kabuto, K.; Sasaki, Y. J. Chem. Soc., Chem. Commun. 1987, 670.
12. (d) Kabuto, K.; Sasaki, Y. Chem. Lett. 1989, 385.
13. (e) Kabuto, K.; Sasaki, Y. Tetrahedron Lett. 1990, 31, 1031.
14. (f) Hazama, R.; Umakoshi, K; Kabuto, C.; Kabuto, K.; Sasaki, Y. J. Chem. Soc., Chem. Commun. 1996, 15.
15. Morrill T. C. In Methods in Stereochemical Analysis; Marchand, A. P, Ed.; VCH Publishers: Weinheim, 1986; Vol. 5, Chapter 1, p 1.
16. Sweeting, L. M.; Crans, D. C.; Whitesides, G. M. J. Org. Chem. 1987, 52, 2273, and references therein.
17. For example: (a) Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081.
18. (b) Eliseev, A. V.; Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1331.
19. (c) Tabushi, I. Ace. Chem. Res. 1982, 75, 66.
20. (d) Saenger, W. Angew. Chem., Int. Ed. Engl. 1980, 19, 344.
21. (e) Breslow, R. Ace. Chem. Res. 1980, 13, 170.
22. For example: (a) Diederich, F. In Cydophanes; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, 1991.
23. (b) Murakami, Y.; Kikuchi, J.; Ohno, T.; Hayashida, O.; Kojima, M. J. Am. Chem. Soc. 1990, 112, 7672.
24. (c) Kikuchi, J.; Egami, K; Suehiro, K.; Murakami, Y. Chem. Lett. 1992, 1685.
25. (d) Odashima, K.; Itai, A.; litaka, Y.; Koga, K. J. Am. Chem. Soc. 1980, 102, 2504.
26. (a) Yanagihara, R.; Tominaga, M.; Aoyama, Y. J. Org. Chem. 1994, 59, 6865.
27. (b) Kobayashi, K.; Asakawa, Y.; Kato, Y.; Aoyama, Y. J. Am. Chem. Soc. 1992, 114, 10307, and references therein.
28. (a) Kobayashi, K.; Tominaga, M.; Asakawa, Y.; Aoyama, Y. Tetrahedron Lett. 1993, 34, 5121.
29. (b) Murakami, Y.; Ohno, T.; Hayashida, O.; Hisaeda, Y. J. Chem. Soc., Chem. Commun. 1991, 950.
30. (a) Carcanague, D. R.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1990, 29, 9, 769.
31. (b) Kumar, S.; Schneider, H.-J. J. Chem. Soc., Perkin Trans. 2 1989, 245.
32. (a) Schneider, H.-J.; Blatter, T.; Palm, B.; Pfingstag, U.; Rüdiger, V.; Theis, I. J. Am. Chem. Soc. 1992,114, 7704.
33. (b) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417.
34. (c) Hosseini, M. W.; Blacker, A. J.; Lehn, J.-M. J. Am. Chem. Soc. 1990, 112, 3896.
35. (a) Chen, H.; Ogo, S.; Fish, R. H. J. Am. Chem. Soc. 1996, 118, 4993.
36. (b) Chen, H.; Maestre, M. F.; Fish, R. H. J. Am. Chem. Soc. 1995, 117, 3631.
37. Smith, D. P.; Baralt, E.; Morales, B.; Olmstead, M. M.; Maestre, M. F.; Fish, R. H. J. Am. Chem. Soc. 1992, 114, 10647.
38. Foster, R.; FYFE, C. A. Prog. Nucl. Magn. Reson. Spectrosc. 1969, 4, 1.