Controlling Diaza-Cope Rearrangement Reactions with Resonance-Assisted Hydrogen Bonds

Journal of the American Chemical Society

Volumn 125, Issue 50, 2003, Pages 15276-15277

  Chin, Jik ^a,b   Mancin, Fabrizio ^a,b   Thavarajah, Nirusha ^a,b   Lee, Donghyung ^a,b   Lough, Alan ^a,b   Chung, Doo Soo ^a,b  

^a Department of Chemistry ^*  (Canada)

^b Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE DERIVATIVE; HETEROCYCLIC COMPOUND;

ARTICLE; CALCULATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLIZATION; GEOMETRY; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0346850032     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0387554     Document Type: Article

References (20)

1. Cleland, W. W.; Kreevoy, M. M. Science (Washington, DC) 1994, 264, 1887-1890.
2. Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science (Washington, DC) 1994, 264, 1927-1930.
3. Guthrie, J. P. Chem. Biol. 1996, 3, 163-170.
4. Shan, S.-o.; Loh, S.; Herschlag D. Science (Washington, DC) 1996, 272, 97-101.
5. Warshel, A.; Papazyan, A.; Kollman, P. A. Science (Washington, DC) 1995, 269, 102-104.
6. Gilli, G.; Bellucci, F.; Ferretti, V.; Bertolasi, V. J. Am. Chem. Soc. 1989, 111, 1023-1028.
7. Bertolasi, V.; Gilli, P.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 1991, 113, 4917-4925.
8. Vögtle, F.; Goldschmitt, E. Chem. Ber. 1976, 109, 1-40.
9. Vögtle, F.; Goldschmitt, E. Angew. Chem., Int. Ed. Engl. 1974, 13, 480.
10. Vögtle, F.; Goldschmitt, E. Angew. Chem., Int. Ed. Engl. 1973, 12, 767.
11. Chin, J.; Chung, S.; Kim, D. H. J. Am. Chem. Soc. 2002, 124, 10948-10949.
12. Mancin, F.; Chin, J. J. Am. Chem. Soc. 2002, 124, 10946-10947.
13. 3, Z = 2; Final R indices [I > 2σ(I)], R1 = 0.0489, wR2 = 0.1171; R indices (all data) R1 = 0.0717, wR2 = 0.1312.
14. Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 2000, 124, 10405-10417.
15. Filarowski, A.; Koll, A.; Glowiak, T. J. Chem. Soc., Perkin Trans. 2 2002. 835-842.
16. 0→298 K) from 0 K to 298 K and at 1 atm were obtained form vibrational frequencies.
17. Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580-2627.
18. Bemhardt, G.; Gust, R.; Reile, H.; Vom Orde, H. D.; Mueller, R.; Keller, C.; Spruss, T.; Schoenenberger, H.; Burgemeister, T. J. Cancer Res. Clin. Oncol. 1992, 118, 201-208.
19. Corey, E. J.; Kuhnle, F. N. M. Tetrahedron Lett. 1997, 38, 8631-8634.
20. Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science (Washington, DC) 1997, 277, 936-938.