Redox-induced conformational alteration of N,N-diarylamides

Organic Letters

Volumn 9, Issue 26, 2007, Pages 5545-5547

  Okamoto, Iwao ^a   Yamasaki, Ryu ^b   Sawamura, Mika ^a   Kato, Takako ^c   Nagayama, Naomi ^a   Takeya, Tetsuya ^a   Tamura, Osamu ^a   Masu, Hyuma ^c   Azumaya, Isao ^c   Yamaguchi, Kentaro ^c   Kagechika, Hiroyuki ^d   Tanatani, Aya ^e,f  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^d TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^e OCHANOMIZU UNIVERSITY   (Japan)

^f JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; OXIDATION REDUCTION REACTION;

AMIDES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXIDATION-REDUCTION;

EID: 38349174496     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702504x     Document Type: Article

References (30)

1. (a) Balzani, V.; Credi, A.; Venturi, M. Molecular Devices and Machines; Wiley-VCH: Weinheim, Germany, 2004.
2. (b) Feringa, B. L., Ed. Molecular Switches: Wiley-VCH: Weinheim, Germany, 2001.
3. (a) Clayden, J.; Lund, A.; Vallverdú, L.; Helliwell, M. Nature 2004, 431, 966-971.
4. (b) Kern, D.; Zuiderweg, E. R. P. Curr. Opin. Struct. Biol. 2003, 13, 748-757.
5. (c) Seebach, D.; Schreiber, J. V.; Abele, S.; Daura, X.; van Gunsteren, W. F. Helv. Chim. Acta 2000, 83, 34-57.
6. (a) Feringa, B. L. Acc. Chem. Res. 2001, 34, 504-513.
7. (b) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348-3391.
8. (c) Irie, M., Ed. Chem. Rev. 2000, 100, 1683-1890.
9. (a) Kanazawa, H.; Higuchi, M.; Yamamoto, K. J. Am. Chem. Soc. 2005, 127, 16404-16405.
10. (b) Kim, H. G.; Lee, C.-W.; Yun, S.; Hong, B. H.; Kim, Y.-O.; Kim, D.; Ihm, H.; Lee, J. W.; Lee, E. C.; Tarakeshwar, P.; Park, S.-M.; Kim, K. S. Org. Lett. 2002, 4, 3971-3974.
11. (c) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Venturi, M. Acc. Chem. Res. 2001, 34, 445-455.
12. (d) Collin, J.-P.; Dietrich-Buchecker, C.; Gaviña, P.; Jimenez-Molero, M. C.; Sauvage, J.-P. Acc. Chem. Res. 2001, 34, 477-487.
13. The amide linkage: Structural significance in chemistry, biochemistry, and materials science; Greenberg, A., Breneman, C. M., Liebman, J. F., Eds.; John Wiley & Sons: New York, 1999.
14. Yamasaki, R.; Tanatani, A.; Azumaya, I.; Saito, S.; Yamaguchi, K.; Kagechika, H. Org. Lett. 2003, 5, 1265-1267.
15. Yamasaki, R.; Tanatani, A.; Azumaya, I.; Masu, H.; Yamaguchi, K.; Kagechika, H. Cryst. Growth Des. 2006, 6, 2007-2010.
16. (a) Okamoto, I.; Nabeta, M.; Hayakawa, Y.; Morita, N.; Takeya, T.; Masu, H.; Azumaya, I.; Tamura, O. J. Am. Chem. Soc. 2007, 129, 1892-1893.
17. (b) Okamoto, I.; Nabeta, M.; Minami, T.; Nakashima, A.; Morita, N.; Takeya, T.; Masu, H.; Azumaya, I.; Tamura, O. Tetrahedron Lett. 2007, 48, 573-577.
18. (c) Okamoto, I.; Nabeta, M.; Yamamoto, M.; Mikami, M.; Takeya, T.; Tamura, O. Tetrahedron Lett. 2006, 47, 7143-7146.
19. The dihedral angles between the amide plane and the dioxyphenyl and phenyl planes were 80.61° and 62.45° for 1, 88.72° and 80.09° for 2, and 65.11° and 77.80° for 3, respectively.
20. Saito, S.; Toriumi, Y.; Tomioka, N.; Itai, A. J. Org. Chem. 1995, 60, 4715-4720.
21. 8 at 168 K, thus 3 exists in (Z)-amide form predominantly (96%).
22. (a) Uno, B.; Okumura, N.; Goto, M.; Kano, K. J. Org. Chem. 2000, 65, 1448-1455.
23. (b) Egeland, R. D.; Marken, F.; Southern, E. M. Anal. Chem. 2002. 74, 1590-1596.
24. (c) Bäckvall, J.-E.; Gogoll, A. J. Chem. Soc., Chem. Commun. 1987, 1236-1238.
25. (d) Kimura, M.; Kaneko, Y. J. Chem. Soc., Dalton Trans. 1984, 3, 341-343.
26. Electrochemical oxidation was performed in a solution of 0.1 M tetra-n-butylammonium perchlorate in acetonitrile, using platinum mesh as working and counter electrodes, and Ag/AgCl electrodes as the reference for constant potential oxidation. Acetic acid (200 equiv) was added as a proton source. Constant potential reduction was performed similarly.
27. (a) Thepchatri, P.; Eliseo, T.; Cicero, D. O.; Myles, D.; Snyder, J. P. J. Am. Chem. Soc. 2007, 129, 3127-3134.
28. (b) Lee, Y.-S.; Marcu, M. G.; Neckers, L. Chem. Biol. 2004, 11, 991-998.
29. (c) Neckers, L.; Lee, Y.-S. Nature 2003, 425, 357-359.
30. (d) Stebbins, C. E.; Russo, A. A.; Schneider, C.; Rosen, N.; Hartl, F. U.; Pavletich, N. P. Cell 1997, 89, 239-250.