Substituent effects in eight-electron electrocyclic reactions

Journal of Organic Chemistry

Volumn 70, Issue 3, 2005, Pages 1035-1041

  Lecea, Begoña ^a   Arrieta, Ana ^a   Cossío, Fernando P ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CONFORMATIONS; ELECTROCHEMISTRY; MOLECULAR STRUCTURE; PROBABILITY DENSITY FUNCTION; SUBSTITUTION REACTIONS;

ELECTROCYCLIC REACTIONS; SUBSTITUENTS; TRANSITION STRUCTURES;

REACTION KINETICS;

OCTA 1,3,5,7 TETRAENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DENSITY FUNCTIONAL THEORY; ELECTRON; MATHEMATICAL COMPUTING; PHASE TRANSITION; STEREOCHEMISTRY; TEMPERATURE;

EID: 13244252392     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048874h     Document Type: Article

References (57)

1. (a) Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie International: Deerfield Beach, FL, 1970.
2. (b) Fukui, K. Acc. Chem. Res. 1971, 4, 57.
3. (a) Pindur, U.; Schneider, G. H. Chem. Soc. Rev. 1994, 409.
4. (b) Trost, B. M.; Fleming, I.; Paquette, L. A. Comprehensive Organic Synthesis; Pergamon: Oxford, UK, 1991; Vol. 5, pp 675-784.
5. Marvell, E. N. Thermal Electrocyclic Reactions; Academic Press: New York, 1980.
6. Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 395.
7. (a) Houk, K. N. In Strain and Its Implications in Organic Chemistry; de Meijere, A., Blechert, S., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1989; p 25.
8. (b) Niwayama, S.; Kallel, E. A.; Spellmeyer, D. C.; Sheu, C.; Houk, K. N. J. Org. Chem. 1996, 61, 2813.
9. (c) Kirmse, W.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1984, 106, 7989.
10. (d) Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 2099.
11. (e) Dolbier, W. R., Jr.; Korionak, H.; Houk, K. N.; Sheu, C. Acc. Chem. Res. 1996, 29, 471.
12. See for example: (a) Cossío, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) López, S.; Rodríguez, J.; Rey, J. G.; de Lera, A. R. J. Am. Chem. Soc. 1996, 118, 1881. (c) Evanseck, J. D.; Thomas, B. E., IV; Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1995, 60, 7134. (d) Lecea, B.; Arrastia, I.; Arrieta, A.; Roa, G.; Lopez, X.; Arriortua, M. I.; Ugalde, J. M.; Cossío, F. P. J. Org. Chem. 1996, 61, 3070.
13. See for example: (a) Cossío, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) López, S.; Rodríguez, J.; Rey, J. G.; de Lera, A. R. J. Am. Chem. Soc. 1996, 118, 1881. (c) Evanseck, J. D.; Thomas, B. E., IV; Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1995, 60, 7134. (d) Lecea, B.; Arrastia, I.; Arrieta, A.; Roa, G.; Lopez, X.; Arriortua, M. I.; Ugalde, J. M.; Cossío, F. P. J. Org. Chem. 1996, 61, 3070.
14. See for example: (a) Cossío, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) López, S.; Rodríguez, J.; Rey, J. G.; de Lera, A. R. J. Am. Chem. Soc. 1996, 118, 1881. (c) Evanseck, J. D.; Thomas, B. E., IV; Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1995, 60, 7134. (d) Lecea, B.; Arrastia, I.; Arrieta, A.; Roa, G.; Lopez, X.; Arriortua, M. I.; Ugalde, J. M.; Cossío, F. P. J. Org. Chem. 1996, 61, 3070.
15. See for example: (a) Cossío, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (b) López, S.; Rodríguez, J.; Rey, J. G.; de Lera, A. R. J. Am. Chem. Soc. 1996, 118, 1881. (c) Evanseck, J. D.; Thomas, B. E., IV; Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1995, 60, 7134. (d) Lecea, B.; Arrastia, I.; Arrieta, A.; Roa, G.; Lopez, X.; Arriortua, M. I.; Ugalde, J. M.; Cossío, F. P. J. Org. Chem. 1996, 61, 3070.
16. Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682.
17. Thomas, B. E., IV; Evanseck, J. D.; Houk, K. N. J. Am. Chem. Soc. 1993, 115, 4165.
18. Jiao, H.; Schleyer, P. v. R. J. Chem. Soc., Perkin Trans. 2 1994, 407.
19. (a) Paquette, L. A.; Hamme, A. T.; Kuo, L. M.; Doyon, J.; Kreuzholz, R. J. Am. Chem. Soc. 1997, 119, 1242.
20. (b) Paquette, L. A.; Morwich, T. M. J. Am. Chem. Soc. 1997, 119, 1230.
21. (c) Paquette, L. A. Eur. J. Org. Chem. 1998, 1709.
22. (d) Oliva, M.; Domingo, L. R.; Safont, U.-S.; Andres, J.; Castillo, R.; Moliner, V. J. Phys. Org. Chem. 1999, 12, 61.
23. (a) Nicolaou, K. C.; Petasis, N. A. In Strategies and Tactics in Organic Synthesis; Lindberg, T., Ed.; Academic Press: San Diego, CA, 1984; Vol. 1, pp 155-173.
24. (b) Nicolaou, K. C.; Petasis, N. A.; Zipkin, R. E.; Uenishi, J. J. Am. Chem. Soc. 1982, 104, 5555.
25. (c) Nicolaou, K. C.; Petasis, N. A.; Uenishi, J.; Zipkin, R. E. J. Am. Chem. Soc. 1982, 104, 5557.
26. (d) Nicolaou, K. C.; Petasis, N. A.; Zipkin, R. E. J. Am. Chem. Soc. 1982, 104, 5560.
27. Vogt, P.; Schlageter, M.; Widmer, E. Tetrahedron Lett. 1991, 32, 4115.
28. Hayashi, R.; Fernández, S.; Okamura, W. H. Org. Lett. 2002, 4, 851.
29. Beaudry, C. M.; Trauner, D. Org. Lett. 2002, 4, 2221.
30. Moses, J. E.; Baldwin, J. E.; Marquez, R.; Adlington, R. M.; Cowley, A. R. Org. Lett. 2002, 4, 3731.
31. Salem, B.; Suffert, J. Angew. Chem., Int. Ed. 2004, 43, 2826.
32. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford: New York, 1989.
33. (a) Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974.
34. (b) Becke, A. D. J. Chem. Soc. 1993, 98, 5648.
35. (c) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
36. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; pp 76-87 and references therein.
37. 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.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.5; Gaussian, Inc.: Pittsburgh, PA, 1998.
38. Guner, V.; Khuong, K. S.; Leach, A. G.; Lee, P. S.; Bartberger, M. D.; Houk, K. N. J. Phys. Chem. A 2003, 107, 11445.
39. (a) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
40. (b) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
41. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
42. Wolinski, K.; Hilton, J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251.
43. Goldfarb, T.; Lindqvist, L. J. Am. Chem. Soc. 1967, 89, 4588.
44. Wiest, O.; Houk, K. N.; Black, K. A.; Thomas, B. E., IV. J. Am. Chem. Soc. 1995, 117, 8594.
45. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Ya. Aromaticity and Antiaromaticity. Electronic and Structural Aspects; Wiley: New York, 1994; pp 104-115.
46. Morao, I.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1997, 62, 7033.
47. Morao, I.; Cossío, F. P. J. Org. Chem. 1999, 64, 1868.
48. Cossío, F. P.; Morao, I.; Jiao, H.; Schleyer, P. v. R. J. Am. Chem. Soc. 1999, 121, 6737.
49. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Clarendon Press: Oxford, UK, 1990; pp 13-52.
50. Collard, K.; Hall, G. C. Int. J. Quantum Chem. 1977, 12, 623. For other crowded structures involving unusual critical points of electron density see for example: Mixon, S. T.; Cioslowski, J. J. Am. Chem. Soc. 1991, 113, 6760.
51. Collard, K.; Hall, G. C. Int. J. Quantum Chem. 1977, 12, 623. For other crowded structures involving unusual critical points of electron density see for example: Mixon, S. T.; Cioslowski, J. J. Am. Chem. Soc. 1991, 113, 6760.
52. The computed NICS for both ring points of TSa is -9.901 ppm, a value quite similar to that obtained for the cage point. However, we think that this latter point is more appropriate to describe the aromaticity of this transition structure because it is unique and is at the center of the cyclic structure.
53. De Lera, A. R.; Alvarez, R.; Lecea, B.; Torrado, A.; Cossío, F. P. Angew. Chem., Int. Ed. 2001, 40, 557.
54. Pauling, L. The Nature of the Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, UK, 1960; p 224.
55. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
56. (a) Huisgen, R.; Dahmem, A.; Huber, H. Tetrahedron Lett. 1969, 1461.
57. (b) Huisgen, R.; Dahmem, A.; Huber, H. J. Am. Chem. Soc. 1967, 89, 7130.