Nitrosation of amides involves a pseudopericyclic 1,3-sigmatropic rearrangement

Organic Letters

Volumn 6, Issue 5, 2004, Pages 851-854

  Birney, David M ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FORMAMIDE; N METHYLFORMAMIDE; NITROSAMINE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CURTIUS REARRANGEMENT; NITROSATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 1642293994     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049867i     Document Type: Article

References (33)

1. Wang, P. G.; Xian, M.; Tang, X.; Wu, X.; Wen, Z.; Cai, T.; Janczuk, A. J. Chem. Rev. 2002, 102, 1091-1134.
2. Gnewuch, C. T.; Sosnovsky, G. Chem. Rev. 1997, 97, 829-1013.
3. Kirsch, M.; Korth, H.-G.; Sustmann, R.; de Groot, H. Biol. Chem. 2002, 383, 389-399 and references therein.
4. (a) Kim, S.; Ponka, P. Blood Cells, Mol. Dis. 2002, 29, 400-410.
5. (b) Kaur, H.; Hughes, M. N.; Green, C. J.; Naughton, P.; Foresti, R.; Motterlini, R. FEBS Lett. 2003, 543, 113-119 and references therein.
6. (a) Turjanski, A. G.; Leonik, F.; Estrin, D. A.; Rosenstein, R. E.; Doctorovich, F. J. Am. Chem. Soc. 2000, 122, 10468-10469.
7. (b) Darbeau, R. W.; Pease, R. S.; Perez, E. V. J. Org. Chem. 2002, 67, 2942-2947 and references therein.
8. (a) Zyryanov, G. V.; Rudkevich, D. M. Org. Lett. 2003, 5, 1253-1256.
9. (b) Zyryanov, G. V.; Kang, Y.; Rudkevich, D. M. J. Am. Chem. Soc. 2003, 125, 2997-3007.
10. Rosokha, S. V.; Lindeman, S. V.; Rathore, R.; Kochi, J. K. J. Org. Chem. 2003, 68, 3947-3957.
11. Gwaltney, S. R.; Rosokha, S. V.; Head-Gordon, M.; Kochi, J. K. J. Am. Chem. Soc. 2003, 125, 3273-3283.
12. (a) Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie, GmbH: Weinheim, 1970.
13. (b) Berson, J. A. Acc. Chem. Res. 1972, 5, 406-414.
14. (c) Berson, J. A.; Holder, R. W. J. Am. Chem. Soc. 1973, 95, 2037-2038.
15. (d) Carpenter, B. K. J. Am. Chem. Soc. 1995, 117, 6336-6344.
16. (a) Birney, D. M. J. Org. Chem. 1996, 61, 243-251.
17. (b) Birney, D. M.; Xu, X.; Ham, S. Angew. Chem., Int. Ed. 1999, 38, 189-193.
18. (c) Zhou, C.; Birney, D. M. J. Am. Chem. Soc. 2002, 124, 5231-5241.
19. (a) Snyder, J. P.; Halgren, T. A. J. Am. Chem. Soc. 1980, 102, 2861-2863.
20. (b) Fraser-Reid, B.; Tulshian, R. T. D. B.; Sun, K. M. J. Org. Chem. 1981, 46, 6, 3767-3768.
21. (c) Wong, M. W.; Wentrup, C. J. Org. Chem. 1994, 59, 5279-5285.
22. (d) Koch, R.; Wong, M. W.; Wentrup, C. J. Org. Chem. 1996, 61, 6809-6813.
23. (e) Nguyen, M. T.; Landuyt, L.; Nguyen, H. M. T. J. Org. Chem. 1999, 64, 401-407.
24. (f) Ammann, J. R.; Flammang, R.; Wong, M. W.; Wentrup, C. J. Org. Chem. 2000, 65, 2706-2710.
25. (g) Chamorro, E.; Santos, J. C.; Gomez, B.; Contreras, R.; Fuentealba, P. J. Chem. Phys. 2001, 114, 23-34.
26. The B3LYP method ((a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652), the 6-31G(d,p) basis set ((b) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213), and Gaussian 98 were used for the calculations ((c) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998). See Supporting Information for computational details.
27. The B3LYP method ((a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652), the 6-31G(d,p) basis set ((b) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213), and Gaussian 98 were used for the calculations ((c) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998). See Supporting Information for computational details.
28. The B3LYP method ((a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652), the 6-31G(d,p) basis set ((b) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213), and Gaussian 98 were used for the calculations ((c) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998). See Supporting Information for computational details.
29. There has been considerable discussion regarding the importance of amide resonance. For a leading reference, see: Rablen, P. R.; Bentrup, K. H. J. Am. Chem. Soc. 2003, 125, 2142-2147.
30. Doering, W. v. E.; Toscano, V. G.; Beasley, G. H. Tetrahedron 1971, 27.
31. Bürgi, H. B.; Dunitz, J. D. Acc. Chem. Res. 1983, 16, 153-161.
32. We thank a referee for suggesting this aspect of the study.
33. act); barriers in solution are slightly higher. Ross, B. D.; True, N. S.; Matson, G. B. J. Phys. Chem. 1984, 88, 2675-2678.