Mechanisms of tetrazole formation by addition of azide to nitriles

Journal of the American Chemical Society

Volumn 124, Issue 41, 2002, Pages 12210-12216

  Himo, Fahmi ^a   Demko, Zachary P ^a   Noodleman, Louis ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NEGATIVE IONS; PROBABILITY DENSITY FUNCTION; REACTION KINETICS;

CYCLOADDITION;

NITROGEN COMPOUNDS;

ANION; AZIDE; NITRILE; TETRAZOLE DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL REACTION; CORRELATION ANALYSIS; CYCLIZATION; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; HYBRID; REACTION ANALYSIS; TEMPERATURE DEPENDENCE; THEORY;

EID: 0037120838     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0206644     Document Type: Article

References (48)

1. Butler, R. N. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, U.K., 1996; Vol. 4.
2. A simple search of the MDDR database (6/01) provided 173 1-alkylated and 151 2-alkylated 5-C-tetrazoles and 147 1-alkylated and 33 2-alkylated 5-heterotetrazoles.
3. Singh, H.; Chawla, A. S.; Kapoor, V. K.; Paul, D.; Malhotra, R. K. Prog. Med. Chem. 1980. 17, 151-183.
4. Ostrovskii, V. A.; Pevzner, M. S.; Kofmna, T. P.; Shcherbinin, M. B.; Tselinskii, I. V. Targets Heterocycl. Syst. 1999, 3, 467-526.
5. Hiskey, M.; Chavez, D. E.; Naud, D. L.; Son, S. F.; Berghout, H. L.; Bome, C. A. Proc. Int. Pyrotech. Semin. 2000, 27, 3-14.
6. Koldobskii, G. I.; Ostrovskii, V. A. Usp. Khim. 1994, 63, 847-865.
7. (a) Huisgen, R.; Sauer, J.; Sturm, H. J.; Markgraf, J. H. Chem. Ber. 1960, 93, 2106-2124.
8. (b) Moderhack, D. J. Prakt. Chem. 1988, 340, 687-709.
9. (a) Quast, H; Bieber, L., Tetrahedron Lett. 1976, 18, 1485-1486.
10. (b) Krayushin, M. M.; Beskopylnyi A. M., Zlotin, S. G.; Lukyanov, O. A.; Zhulin, V. M. Izv. Akad. Nauk. SSSR Ser. Khim. 1980, 11, 2668.
11. (c) Zavarzin, I. V.; Zhulin, V. M.; Yarovenko, V. N.; Krayushkin, M. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1988, 5, 1168-1170.
12. (d) Klaubert, D. H.; Sellstedt, J. H.; Guinosso, C. J.; Bell, S. C.; Capetola, R. J. J. Med. Chem. 1981, 24, 748-752.
13. (e) Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 12, 2110-2113.
14. (f) Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 12, 2113-2116.
15. Carpenter, W. R. J. Org. Chem. 1962, 27, 2085-2088.
16. Huisgen, R. J. Org. Chem. 1968, 33, 2291-2297.
17. Dimroth, O.; Fester, G. Chem. Ber. 1910, 43, 2219-2223.
18. (a) Dunica, J. V.; Pierce, M. E.; Santella, J. B., III J. Org. Chem. 1991, 56, 2395-2400.
19. (b) Wittenberger, S. J.; Donner, B. G. J. Org. Chem. 1993, 58, 4139-4141.
20. (c) Curran, D. P.; Hadida, S.; Kim, S.-Y. Tetrahedron 1999, 55, 8997-9006.
21. (d) Wiberg, V. E.; Michaud, H. Z. Naturforsch. B 1954, 9, 496-497.
22. (e) Grzonka, Z.; Liberek, B. Rocz. Chem. 1971, 45, 967-980.
23. (f) Huff, B. E.; Staszak, M. A. Tetrahedron Lett. 1993, 34, 8011-8014.
24. (g) Kumar, A.; Narayanan, R; Shechter, H. J. Org. Chem. 1996, 61, 4462-4465.
25. (h) Gallante, R. J. U.S. Patent 5,502,191, 1995.
26. (i) Demko, Z. P.; Sharpless, K. B. J. Org. Chem. 2001, 66, 7945-7950.
27. Finnegan, W. G.; Henry, R. A.; Lofquist, R. J. Am. Chem. Soc. 1958, 80, 3908-3911.
28. Jursic, E.; Zdravkovski, Z. THEOCHEM 1994, 118, 11-22.
29. (a) Titova, I. E.; Poplavskii, V. S.; Koldobskii, G. I.; Ostrovskii, V. A.; Nikolaev, V. D.; Erusalimskii, G. B. Khim. Geterosikl. Soedin. 1986, 8, 1086-1089.
30. (b) Ostrovskii, V. A.; Poplavskii, V. S.; Koldobskii, G. I.; Emsalimskii, G. B. Khim. Geterosikl. Soedin. 1992, 9, 1214-1217.
31. Demko, Z. P.; Sharpless, K. B. Org. Lett. 2001, 3, 4091-4094, Scheme 2.
32. Sullivan, M. J.; Kilpatrick, M. L. J. Am. Chem. Soc. 1945, 67, 1815-1823.
33. (a) Pinner, A. Die Imidoäther und ihre Derivate; Oppenheim: Berlin, 1892.
34. (b) Ritter, J. J.; Tillmanns, E. J. J. Org. Chem. 1957, 22, 839-840.
35. (c) Schaefer, F. C. In The Chemistry of the Cyano Group; Rappoport, Z., Ed.; Interscience: London, 1970; Chapt. 6.
36. Wittenberger, S. J. Org. Prep. Proced. Int. 1994. 26, 499-531.
37. Koguro, K.; Oga, T.; Mitsui, S.; Orita, R. Synthesis 1998, 910-914.
38. (a) Becke, A. D. Phys. Rev. 1988, A38, 3098-3100.
39. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377.
40. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
41. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson. P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen. M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian 98, Revision A.9; Gaussian, Inc.; Pittsburgh. PA, 1998.
42. (a) Barone, V.; Cossi, M. J. Phys. Chem. 1998, 102, 1995-2001.
43. (b) Barone, B.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404-417.
44. Orozco, M.; Luque, F. J. Chem. Rev. 2000, 100, 4187-4226.
45. Sadlej-Sosnowska, N. J. Org. Chem. 2001, 66, 8737-8743, and references therein.
46. Sauer, J.; Huisgen, R.; Strum, H. J. Tetrahedron 1960, 11, 241-251.
47. - is in place here. Negatively charged molecules of this small size tend usually to be undersolvated with the methods used here. This would mean that the barriers calculated here are somewhat underestimated. However, since the error is constant, this should not affect relative barriers.
48. Kollman, P. A.; Kuhn, B.; Peräkylä. M. J. Phys. Chem. 2002, 106, 1537-1542.