Toward an understanding of the unexpected regioselective Hetero-Diels-Alder reactions of asymmetric tetrazines with electron-rich ethylenes: A DFT study

Journal of Organic Chemistry

Volumn 74, Issue 7, 2009, Pages 2726-2735

  Domingo, Luis R ^a   Picher, M Teresa ^a   Sáez, José A ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CONSECUTIVE REACTIONS; DFT METHODS; DFT STUDIES; DOMINO PROCESS; ELECTRON DENSITIES; ELECTRON-RICH; HETERO DIELS ALDERS; HETERO-DIELS-ALDER REACTIONS; HYDROGEN ELIMINATIONS; PARA POSITIONS; REGIO-SELECTIVE; RETRO-DIELS-ALDER REACTIONS; TETRAZINES;

CHARGE TRANSFER; DIRECTIVE ANTENNAS; HYDROGEN; ION EXCHANGE; PROBABILITY DENSITY FUNCTION; REGIOSELECTIVITY;

ETHYLENE;

ETHYLENE DERIVATIVE; PYRIDAZINE DERIVATIVE; TETRAZINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; ELECTRON;

EID: 64249090422     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802822u     Document Type: Article

References (50)

1. (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, CA, 1987.
2. (b) Sauer, J. Comprehensive Heterocyclic Chemistry II; Pergamon: London, UK, 1996; Vol. 6, pp 901-965.
3. (c) Boger, D. L.; Coleman, R. S.; Panek, J. P.; Huber, F. X.; Sauer, J. J. Org. Chem. 1985, 50, 5377-5379.
4. (d) Warrener, R. N.; Margetic, D.; Amarasekara, A. S.; Butler, D. N.; Mahadevan, I. B.; Russell, R. A. Org. Lett. 1999, 1, 199-202.
5. (e) Yeung, B. K. S.; Boger, D. L. J. Org. Chem. 2003, 68, 5249-5253.
6. Soenen, D. R.; Zimpleman, J. M.; Boger, D. L. J. Org. Chem. 2003, 68, 3593-3598.
7. Boger, D. L.; Hong, J. J. Am. Chem. Soc. 2001, 123, 8515-8519.
8. Boger, D. L.; Sakya, S. M. J. Org. Chem. 1988, 53, 1415-1423.
9. Boger, D. L.; Schaum, R. P.; Garbaccio, R. M. J. Org. Chem. 1998, 63, 6329-6337.
10. Hamasaki, A.; Ducray, R.; Boger, D. L. J. Org. Chem. 2006, 71, 185-193.
11. Cioslowski, J.; Sauer, J.; Hetzenegger, J.; Karcher, T.; Hierstetter, T. J. Am. Chem. Soc. 1993, 115, 1353-1359.
12. Sadasivam, D. V.; Prasad, E.; Flowers, R. A.; Birney, D. M. J. Phys. Chem. A 2006, 110, 1288-1294.
13. Gomez-Bengoa, E.; Helm, M. D.; Plant, A.; Harrity, J. P. A. J. Am. Chem. Soc. 2007, 129, 2691-2699.
14. Domingo, L. R.; Aurell, M. J.; Perez, P.; Contreras, R. J. Org. Chem. 2003, 68, 3884-3890.
15. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
16. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
17. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986.
18. (a) Schlegel, H. B. Geometry Optimization on Potential Energy Surface. In Modern Electronic Structure Theory; Yarkony, D. R., Ed.; World Scientific Publishing: Singapore, 1994.
19. (b) Schlegel, H. B. J. Comput. Chem. 1982, 3, 214-218.
20. Fukui, K. J. Phys. Chem. 1970, 74, 4161-4163.
21. (a) Gonzalez, J.; Houk, K. N. J. Org. Chem. 1992, 57, 3031-3037.
22. (b) Gonzalez, J.; Taylor, E. C.; Houk, K. N. J. Org. Chem. 1992, 57, 3753-3755.
23. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
24. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
25. (b) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746.
26. Frisch, M. J.; et al. Gaussian 03, Revision C.02; Gaussian, Inc., Wallingford, CT, 2004.
27. (a) Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094.
28. (b) Simkin, B. Y.; Sheikhet, I. Quantum Chemical and Statistical Theory of Solutions-A Computational Approach; Ellis Horwood: London, UK, 1995.
29. (a) Cances, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032-3041.
30. (b) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327-335.
31. (c) Barone, V.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404-417.
32. Parr, R. G.; von Szentpaly, L.; Liu, S. J. Am. Chem. Soc. 1999, 121, 1922-1924.
33. (a) Parr, R. G.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512-7516.
34. (b) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
35. Domingo, L. R.; Chamorro, E.; Pérez, P. J. Org. Chem. 2008, 73, 4615-4624.
36. Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, 1133-1138.
37. (a) Geerlings, P.; De Proft, F.; Langenaeker, W. Chem. Rev. 2003, 103, 1793-1873.
38. (b) Ess, D. H.; Jones, G. O.; Houk, K. N. Adv. Synth. Catal. 2006, 348, 2337-2361.
39. (a) Domingo, L. R.; Aurell, M. J.; Perez, P.; Contreras, R. Tetrahedron 2002, 58, 4417-4423.
40. (b) Pérez, P.; Domingo, L. R.; Aizman, A.; Contreras, R. In Theoretical Aspects of Chemical Reactivity; Toro-Labbé, A., Ed.; Elsevier Science: Amsterdam, The Netherlands, 2007; Vol. 19, pp 139-201.
41. Jaramillo, P.; Domingo, L. R.; Chamorro, E.; Pérez, P. J. Mol. Struct. (THEOCHEM) 2008, 68-72.
42. Castillo, R.; Andrés, J.; Domingo, L. R. Eur. J. Org. Chem. 2005, 470, 5-4709.
43. (a) Dominso, L. R. J. Org. Chem. 2001, 66, 3211-3214.
44. (b) Arrovo, P.; Picher, M. T.; Domingo, L. R.; Temer, F. Tetrahedron 2005, 61, 73597365
45. Polo, V.; Domingo. L. R.; Andres, J. J. Ore. Chem. 2006. 71, 754-762.
46. Domingo, L. R.; Saéz, J. A.; Zaragoza, R. J.; Arno, M. J. Org. Chem. 2008, 73, 8791-8799.
47. Hammond, G. S. J. Am, Chem. Soc. 1955, 77, 334-338.
48. Wiberg, K. B. Tetrahedron 1968, 24, 1083-1096.
49. Domingo, L. R.; Arno, M.; Andres. J. J. Org. Chem. 1999, 64, 5867-5875.
50. Avers, P. W.; Parr, R. G. J. Am. Chem. Soc. 2000, 122, 2010-2018.