A theoretical investigation on the cycloaddition reaction between azocarbenium ions and nitriles

International Journal of Quantum Chemistry

Volumn 108, Issue 6, 2007, Pages 1067-1075

  Li, Zhi Ming ^a   Wang, Quan Rui ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

3 + 2 cycloaddition; Azocarbenium ion; Density functional theory; Nitriles; Reaction mechanism

Indexed keywords

ACTIVATION ENERGY; DENSITY FUNCTIONAL THEORY; EXCITATION ENERGY; IONS; NITROGEN COMPOUNDS;

[3 + 2]-CYCLOADDITION; AZOCARBENIUM ION; ISODENSITY-SURFACE POLARIZABLE CONTINUUM (IPCM);

CYCLOADDITION;

EID: 40749102135     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.21560     Document Type: Article

References (46)

1. (a) Huisgen, R. J Org Chem 1968, 33, 2291;
2. (b) Huisgen, R. J Org Chem 1976, 41, 403;
3. (c) Houk, K. N.; Firestone, R. A.; Munchausen, L. L.; Mueller, P. H.; Arison, B. H.; Garcia, L. A. J Am Chem Soc 1985, 107, 7227;
4. (d) Su, M.; Liao, H.; Chung, W.; Chu, S. J Org Chem 1999, 64, 6710;
5. (e) Avalos, M.; Babiano, R.; Cintas, P.; Clemente, F. R. Gordillo, R.; Jiménez, J. L.; Palacios, J. C.; Raithby, P. R. J Org Chem 2000, 65, 5089;
6. (e) Liao, H.; Su, M.; Chung, W.; Chu, S. Int J Quantum Chem 2001, 83, 318;
7. (f) Kavitha, K.; Venuvanalingam, P. Int J Quantum Chem 2005, 104, 64;
8. (g) Merino, P.; Tejero, T.; Chiacchio, U.; Romeo, G.; Rescifina, A. Tetrahedron 2007, 63, 1448.
9. (a) Okimoto, M.; Chiba, T. J Org Chem 1990, 55, 1070;
10. (b) Butler, R. N. Chem Rev 1984, 84, 249;
11. (c) Hammerich, O.; Parker, V. D. J Chem Soc Perkin Trans 1 1972, 1718;
12. (d) Gunic, E.; Tabakovic, I. J Org Chem 1988, 53, 5081;
13. (e) Warkentin, J. Synthesis 1970, 279;
14. (f) Lin, E.-C.; Van De Mark, M. R. J Chem Soc Chem Commun 1982, 1176;
15. (g) Crljenak, S.; Tabakovic, I.; Jeremie, D.; Gaon, I. Acta Chem Scand Ser B 1983, 37, 527.
16. Wang, Q.; Jochims, J. C.; Kohlbrandt, S.; Dahlenburg, L.; Al-Taib, M.; Hamed, A.; Ismail, A. E. Synthesis 1992, 710.
17. (a) Wirschun, W.; Jochims, J. C. Synthesis 1997, 233;
18. (b) Wirschun, W.; Winkler, M.; Lutz, K.; Jochims, J. C. J Chem Soc Perkin Trans 1 1998, 1755;
19. (c) Parsons, S.; Passmore, J.; Schriver, M. J.; Sun, X. Inorg Chem 1991, 30, 3342;
20. (d) Burford, N.; Johnson, J. P.; Passmore, J.; Schriver, M. J.; White, P. S. J Chem Soc Chem Commun 1986, 966.
21. Wang, Q.; Amer, A.; Mohr, S.; Ertel, E.; Jochims, J. C. Tetrahedron 1993, 49, 9973.
22. Guo, Y.; Wang, Q.; Jochims, J. C. Synthesis 1996, 274.
23. Wang, Q.; Al-Talib, M.; Jochims, J. C. Chem Ber 1994, 127, 541.
24. Wang, Q.; Amer, A.; Throll, C.; Fischer, H.; Jochims, J. C. Chem Ber 1993, 126, 2519.
25. Wang, Q.; Mohr, S.; Jochims, J. C. Chem Ber 1994, 127, 947.
26. (a) Liu, X.; Liu, Y.; Wang, Q.; Zou, J. Synth Commun 2000, 30, 119;
27. (b) Liu, X.; Wang, Q.; Liu, Y.; Fan, Y.; Ding Z. Synthesis 2000, 435;
28. (c) Wang, Q.; Li, Z.; Yang, H.; Li, F.; Ding, Z.; Tao, F. Synthesis 2003, 1231;
29. (d) Li, Z.; Wang, Q.; Tao, F. Synth Commun 2004, 34, 1691;
30. (e) Li, Z.; Meng, Q.; Wang, Q.; Tao, F. Chin J Chem 2004, 22, 290.
31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E., Jr.; 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.; Baboul, A. G.; 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.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A. 7; Gaussian: Pittsburgh, PA, 1998.
32. (a) Becke, A. D.; Phys Rev A 1988, 38, 3098;
33. (b) Lee, C.; Yang, W.; Parr, R. G. Phys Rev B 1988, 37, 785;
34. (c) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem Phys Lett 1989, 157, 200;
35. (d) Becke, A. D. J Chem Phys 1993, 98, 5648.
36. (a) Gauss, J.; Cremer, C. Chem Phys Lett 1988, 150, 280;
37. (b) Salter, E. A.; Trucks, G. W.; Bartlett, R. J. J Chem Phys 1989, 90, 1752.
38. Lee, T. J.; Scuseria, G. In Quantum Mechanical Electronic Structure Calculations with Chemical Accuracy; Langnoff, S. F., Ed.; Kluwer Academic Press: Dordrecht, The Netherlands, 1995.
39. (a) Gonzalez, C.; Schlegel, H. B. J Chem Phys 1989, 90, 2154;
40. (b) Gonzalez, C.; Schlegel, H. B. J Phys Chem 1990, 94, 5523.
41. Foresman, J. B.; Keith, T. A.; Wieberg, K. B.; Snoonian, J.; Frisch, M. J. J Phys Chem 1996, 100, 16098.
42. Wei, M. J.; Fang, D. C.; Liu, R. Z. J Org Chem 2002, 67, 7432.
43. Wei, M. J.; Fang, D. C.; Liu, R. Z. E J Org Chem 2004, 19, 4070.
44. Dean, J. A. Lange's Handbook of Chemistry, 15th ed.; McGraw-Hill: New York, 1998; Chapter 4, 4.42.
45. (a) Kroemer, R. T.; Gstach, H.; Liedl, K. R.; Rode, B. M. J Am Chem Soc 1994, 116, 6277;
46. (b) Kroemer, R. T.; Gstach, H.; Liedl, K. R.; Rode, B. M. J Chem Soc Perkin Trans 2 1994, 2129.