Influence of reactant polarity on the course of the inverse-electron- demand Diels-Alder reaction. A DFT study of regio- and stereoselectivity, presence of Lewis acid catalyst, and inclusion of solvent effects in the reaction between nitroethene and substituted ethenes

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 5867-5875

  Domingo, Luis R ^a   Arnó, Manuel ^a   Andrés, Juan ^b  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITAT JAUME I   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE; PROPYLENE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; ELECTRIC POTENTIAL; ELECTRON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033529818     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990331y     Document Type: Article

References (88)

1. (a) Hammer, J. 1,4-Cycloaddition Reactions, the Diels-Alder in Heterocyclic Synthesis; Academic Press: New York, 1967.
2. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: Orlando, FL, 1987.
3. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990.
4. (d) Oppolzer, W.; Weinreb, S. M.; Boger, D. L.; Roush, W. R. Comprehensive Organic Synthesis: Combining C-C p-Bonds; Pergamon Press: Oxford, 1991; Vol. 5, Chapters 4.1-4.4.
5. (a) Dewar, M. J. S.; Olivella, S.; Stewart, J. J. P. J. Am. Chem. Soc. 1986, 108, 5771.
6. (b) Bach, R. D.; MacDouall, J. J. W.; Schlegel, H. B.; Wolber, G. C. J. Org. Chem. 1989, 54, 2931.
7. (c) Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682.
8. (d) Houk, K. N.; González, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81.
9. (a) Bernardi, F.; Bottoni, A.; Field, M. J.; Guest, M. F.; Hillier, I. H.; Robb, M. A.; Venturini, A. J. Am. Chem. Soc. 1988, 110, 3050.
10. (b) Tietze, L. F.; Fennen, J.; Anders, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 1371.
11. (c) Tran Hau Dau, M. E.; Flament, J.-P.; Lefour, J.-M.; Riche, C.; Grierson, D. S. Tetrahedron Lett. 1992, 33, 2343.
12. (d) Coxon, J. M.; McDonald, D. Q. Tetrahedron Lett. 1992, 33, 3673.
13. (e) Jursic, B. S.; Zdravkovski, Z. J. Chem. Soc., Perkin Trans. 2 1994, 1877.
14. (f) Jursic, B. S.; Zdravkovski, Z. THEOCHEM 1994, 90.
15. (g) Carpenter, J. E.; Sosa, C. P. THEOCHEM 1994, 311, 325.
16. (h) Suarez, D.; Gonzalez, J.; Sordo, T. L.; Sordo, J. A. J. Org. Chem. 1994, 59, 8085.
17. (i) Storer, J. W.; Raimondi, L.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 9675.
18. (a) Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley and Sons: New York, 1976.
19. (b) Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 778.
20. (a) Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc. 1991, 113, 1713.
21. (b) Markó, I. E.; Evans, G. R. Tetrahedron Lett. 1994, 35, 2767.
22. (c) Pugnaud, S.; Masure, D.; Hallé, J.-C.; Chaquin, P. J. Org. Chem. 1997, 62, 8687.
23. (d) Liu, J.; Niwayama, S.; You, Y.; Houk, K. N. J. Og. Chem. 1998, 63, 1064.
24. (a) Sustmann, R.; Sicking, W. J. Am. Chem. Soc. 1996, 118, 12562.
25. (b) Sustmann, R.; Tappanchai, S.; Bandmann, H. J. Am. Chem. Soc. 1996, 118, 12555.
26. Domingo, L. R.; Picher, M. T.; Zaragozá, R. J. J. Org. Chem. 1998, 63, 9183.
27. Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
28. (a) Denmark, S. E.; Cramer, C. J.; Sternberg, J. A. Helv. Chim. Acta 1986, 69, 1971.
29. (b) Denmark, S. E.; Moon, Y.-C.; Cramer, C. J.; Dappen, M. S.; Senanayake, C. B. W. Tetrahedron 1990, 46, 7373.
30. Bäckvall, J.-E.; Karlsson, U.; Chinchilla, R. Tetrahedron Lett. 1991, 32, 5607.
31. Risaliti, A.; Forchiassin, M.; Valentin, E. Tetrahedron 1968, 24, 1889.
32. (a) Domingo, L. R.; Jones, R. A.; Picher, M. T.; Sepúlveda-Arqués, J. Tetrahedron 1995, 51, 8739.
33. (b) Domingo, L. R.; Picher, M. T.; Andrés, J.; Moliner, V.; Safont, V. S. Tetrahedron 1996, 52, 10693.
34. (c) Domingo, L. R.; Picher, M. T.; Andrés, J.; Safont, V. S. J. Org. Chem. 1997, 62, 1775.
35. (a) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
36. (b) Ziegler, T. Chem. Rev. 1991, 91, 651.
37. (a) Stanton, R. V.; Merz, K. M. J. Chem. Phys. 1994, 100, 434.
38. (b) Baker, J.; Muir, M.; Andzelm, J. J. Chem. Phys. 1995, 102, 2036.
39. (c) Jursic, B.; Zdravkovski, Z. J. Chem. Soc., Perkin Trans. 2 1995, 1223.
40. (d) Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036.
41. (e) Branchadell, V. Int. J. Quantum Chem. 1997, 61, 381.
42. (f) Sbai, A.; Branchadell, V.; Ortuño, R. M.; Oliva, A. J. Org. Chem. 1997, 62, 3049.
43. (g) Branchadell, V.; Font, J.; Moglioni, A. G.; Ochoa de Echaguen, C.; Oliva, A.; Ortuno, R. M.; Veciana, J.; Vidai Gancedo, J. J. Am. Chem. Soc. 1997, 119, 9992.
44. (h) Domingo, L. R.; Arno, M.; Andrés, J. J. Am. Chem. Soc. 1998, 120, 1617.
45. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
46. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
47. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986.
48. (a) Schlegel, H. B. J. Comput. Chem. 1982, 3, 214
49. (b) Schlegel, H. B. Geometry Optimization on Potential Energy Surface. in Modern Electronic Structure Theory; Yarkony, D. R., Ed.; World Scientific Publishing: Singapore, 1994.
50. (a) McIver, J. W. J.; Komornicki., A. J. Am. Chem. Soc. 1972, 94, 2625.
51. (b) McIver, J. W. J. Acc. Chem. Res. 1974, 7, 72.
52. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995.
53. (a) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
54. (b) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
55. Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, 1996.
56. (a) Branchadell, V.; Oliva, A.; Bertrán, J. THEOCHEM 1985, 113, 197.
57. (b) Branchadell, V.; Oliva, A.; Bertrán, J. THEOCHEM 1985, 120, 85.
58. (c) Branchadell, V.; Oliva, A.; Bertrán, J. THEOCHEM 1986, 120, 117.
59. (d) Domingo, L. R.; Picher, M. T.; Andrés, J. J. Phys. Org. Chem. 1999, 12, 24.
60. (a) Jursic, B. S.; Zdravkovski, Z. J. Org. Chem. 1995, 59, 7732.
61. (b) Yamabe, S.; Dai, T.; Minato, T. J. Am. Chem. Soc. 1995, 117, 10994.
62. (c) Dai, W.-M.; Lau, C. W.; Chung, S. H.; Wu, D.-Y. J. Org. Chem. 1995, 60, 8128.
63. (d) García, J. I.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 1996, 118, 11680.
64. (e) García, J. I.; Martínez-Merino, V.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 1998, 120, 2415.
65. (a) Birney, D. M.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 4127.
66. (b) McCarrick, M. A.; Wu, Y.-D.; Houk, K. N. J. Org. Chem. 1993, 58, 3330.
67. (c) Venturini, A.; Joglar, J.; Fustero, S.; Gonzalez, J. J. Org. Chem. 1997, 62, 3919.
68. (a) Tomasi, J.; Persico, M. Chem. Rev. 1974, 94, 2027.
69. (b) Simkin, B. Y.; Sheikhet, I. Quantum Chemical and Statistical Theory of Solutions-A Computational Approach; Ellis Horwood: London, 1995.
70. (a) Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1990, 112, 4776.
71. (b) Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Chem. Phys. 1991, 95, 8991.
72. David, R. L. CRC Handbook of Chemistry and Physics, 76th ed.; CRC Press: Boca Raton: FL, 1996.
73. Cativiela, C.; García, J. I.; Mayoral, J. A.; Salvatella, L. Chem. Soc. Rev. 1996, 25, 209.
74. Suarez, D.; Sordo, J. A. Chem. Commun. 1998, 385.
75. Kahn, S. D.; Hehre, W. J.; Pople, J. A. J. Am. Chem. Soc. 1987, 109, 1871.
76. (a) Varandas, A. J. C.; Formosinho, S. J. F. J. Chem. Soc., Faraday Trans. 2 1986, 282.
77. (b) Lendvay, G. THEOCHEM 1988, 167, 331.
78. (c) Lendvay, G. J. Phys. Chem. 1989, 93, 4422.
79. (d) Lendvay, G. J. Phys. Chem. 1994, 98, 6098.
80. Wiberg, K. B. Tetrahedron 1968, 24, 1083.
81. (a) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741.
82. (b) Li, C.-J. Chem. Rev. 1993, 93, 2023.
83. (c) Blokzijl, W.; Engberts, J. B. F. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 1545.
84. (a) Blake, J. F.; Jorgensen, W. L. J. Am. Chem. Soc. 1991, 113, 7430.
85. (b) Ruiz-López, M. F.; Assfeld, X.; García, J. I.; Mayoral, J. A.; Salvatella, L. J. Am. Chem. Soc. 1993, 115, 8780.
86. (c) Jorgensen, W. L.; Lim, D.; Blake, J. F.; Severance, D. L. J. Chem. Soc., Faraday Trans. 1994, 90, 1727.
87. (d) Davidson, M. M.; Hillier, I. H.; Hall, R. J.; Burton, N. A. J. Am. Chem. Soc. 1994, 116, 9294.
88. (e) Cativiela, C.; Dillet, V.; García, J. I.; Mayoral, J. A.; Ruiz-López, M. F.; Salvatella, L. THEOCHEM 1995, 331, 37.