Acyclic or long-bond intermediate in the electron-transfer-catalyzed dimerization of 4-methoxystyrene

Journal of Organic Chemistry

Volumn 71, Issue 23, 2006, Pages 8926-8933

  O'Neil, Lauren L ^a   Wiest, Olaf ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; CATALYSIS; HYDROCARBONS; ISOMERIZATION; PROBABILITY DENSITY FUNCTION; REACTION KINETICS;

4-METHOXYSTYRENE; CYCLOADDITION; PROTOTYPICAL REACTION; TRANSIENT ABSORPTION;

DIMERIZATION;

ABSORPTION; ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; DIMERIZATION; ELECTRON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 84961978629     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061745b     Document Type: Article

References (59)

1. For example: Rössler, U.; Blechert, S. Steckhan, E. Tetrahedron Lett. 1999, 40, 7075-7078.
2. (b) Harirchian, B.; Bauld, N. L. J. Am. Chem. Soc. 1989, 111, 1826-1828.
3. (a) Gassman, P. G.; Hershberger, J. W. J. Org. Chem. 1987, 52, 1337-1339.
4. (b) Wang, X. S.; Zhang, B. W.; Cao, Y. J. Photochem. Photobiol. A: Chemistry 1996, 96, 193-198.
5. (a) Sancar, A. Chem. Rev. 2003, 103, 2203-2237.
6. (b) Harrison, C. B.; O'Neil, L. L.; Wiest, O. J. Phys. Chem. A 2005, 109, 7001-7012.
7. Ledwith, A. Acc. Chem. Res. 1972, 5, 133-139.
8. (a) Kojima, M.; Sakuragi, H.; Tokumaru, K. Bull. Chem. Soc. Jpn. 1989, 62, 3863-3868.
9. (b) Kojima, M.; Sakuragi, H.; Tokumaru, K. Tetrahedron Lett. 1981, 22, 2889-2892.
10. (a) Matsubara, C.; Kojima, M. Tetrahedron Lett. 1999, 40, 3439-3442.
11. (b) Brancaleon, L.; Brousmiche, D.; Rao, V. J.; Johnston, L. J.; Ramamurthy, V. J. Am. Chem. Soc. 1998, 120, 4926-4933.
12. (a) Gotoh, T.; Yamamoto, M.; Nishijima, Y. Polym. Bull. (Berlin) 1980, 2, 357-362.
13. (b) Hayashi, K.; Pepper, D. C. Polym. J. 1976, 8, 1-9.
14. Compare also (c) Bauld, N. L.; Gao, D. Polym. Int. 2000, 49, 253-259.
15. E. g.: (a) Kikuchi, T.; Kadota, S.; Yanada, K.; Tanaka, K.; Watanabe, K.; Yoshizaki, M.; Yokoi T.; Shingu, T. Chem. Pharm. Bull. 1983, 31, 1112-1114.
16. (b) Kobayashi, S.; Inaba, K.; Kimura, I.; Kimura, M. Biol. Pharm. Bull. 1998, 21, 346-349.
17. Rodriguez-Evora, Y.; Schepp, N. P. Org. Biomol. Chem. 2005, 3, 4444-4449.
18. (a) Marshall Wilson, E.; Dietz, J. G.; Shepherd, T. A.; Ho, D. M.; Schnapp, K. A.; Elder, R. C.; Watkins, J. W.; Geraci, L. S.; Campana, C. F. J. Am. Chem. Soc. 1989, 111, 1749-1754.
19. (b) Kadota, S.; Tsubono, K.; Makino, K.; Takeshita, M.; Kikuchi, T. Tetrahedron Lett. 1987, 28, 2857-2860
20. (a) Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1986, 108, 7356-7361.
21. (b) Mattes, S. L.; Fand, S. Org. Photochem. 1983, 6, 233-326.
22. (c) Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1983, 105, 1386-1387.
23. (d) Mattes, S. L.; Farid, S. J. Am. Chem. Soc. 1982, 104, 1454-1456.
24. See also: (e) Neunteufel, R. A.; Arnold, D. A. J. Am. Chem. Soc. 1973, 95, 4080-4081.
25. (a) Flory, P. J. J. Am. Chem. Soc. 1937, 59, 241-253.
26. For a detailed discussion of the mechanistic possibilities, compare: (b) Pryor, W. A.; Lasswell, L. D. Adv. Free-Radical Chem 1975, 5, 27-99.
27. (a) Bauld, N. L.; Pabon, R. J. Am. Chem. Soc. 1985, 105, 633-634.
28. (b) Schepp, N. P.; Johnston, L. J. J. Am. Chem. Soc. 1994, 116, 6985-6903.
29. (c) Bauld, N. L. Tetrahedron 1989, 45, 5307-5363.
30. (d) Schepp, N. P.; Johnston, L. J. J. Am. Chem. Soc. 1996, 118, 2872-2881.
31. (e) Schepp, N. P.; Shukla, D.; Sarker, H.; Bauld, N. L. J. Am. Chem. Soc. 1997, 119, 10325-10334.
32. (f) Johnston, L. J.; Schepp, N. P. In: Advances in Electron-Transfer Chemistry Vol.6; Mariano, P. S., Ed.; JAI Press: New York 1996, 41-102.
33. Lewis, F. D.; Kojima, M. J. Am. Chem. Soc. 1988, 110, 8664-8670.
34. Tojo, S.; Toki, S.; Takamuku, S. J. Org. Chem. 1991, 56, 6240-6243.
35. (a) Jungwirth, P.; Carsky, P.; Bally, T. J. Am. Chem. Soc. 1993, 115, 5776-5782
36. (b) Jungwirth, P.; Carsky, P.; Bally, T. J. Am. Chem. Soc. 1993, 115, 5783-5789.
37. Wiest, O. J. Phys. Chem. A 1999, 103, 7907-7911.
38. Weng, H.; Roth, H. J. Org. Chem. 1995, 60, 4136-4145.
39. (a) Caramella, P.; Houk, K. N.; Domelsmith, L. N. J. Am. Chem. Soc. 1977, 99, 4511-4514.
40. (b) Brown, A.; Dewar, M. J. S.; Schoeller, W. J. Am. Chem. Soc. 1977, 99, 5096-5097.
41. (c) Houk, K. N.; González, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81-90.
42. (d) Anh, N. T.; Frison, G.; Solladié-Cavallo, A.; Metzner, P. Tetrahedron 1998, 54, 12841-12852.
43. Clark, T. Handbook of Computational Chemistry; Wiley & Sons: New York, 1985.
44. (a) Khuong, K. S.; Jones, W. H.; Pryor, W. A. Houk, K. N. J. Am. Chem. Soc. 2005, 127, 1265-1277.
45. (b) Northrup, B. H.; Houk, K. N. J. Org. Chem. 2006, 77, 3-13.
46. (a) Wiest, O.; Oxgaard, J.; Saettel, N. J. Adv. Phys. Org. Chem. 2003, 39, 87-109.
47. (b) Donoghue, P. J. Wiest, O. Chem. Eur. J. 2006, 12, 7018-7026
48. Frisch, M. J.; et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford CT, 2004.
49. (a) Miertus, S.; Scrocco, E.; Tomasi, E Chem. Phys. 1981, 55, 117-129.
50. (b) Barone, V.; Cossi, M. J. Chem. Phys. A 1998, 102, 1995-2001.
51. (c) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681.
52. (a) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454-464.
53. (b) Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218-8224.
54. (c) Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439-4449.
55. (d) Burke, K.; Werschnik, J.; Gross, E. K. U. J. Chem. Phys. 2005, 123, 62206-62215.
56. Hirata, S.; Head-Gordon, M.; Szczepanski, J.; Vala, M. J. Phys. Chem. A 2003, 107, 4940-4951.
57. Cossi, M.; Barone, V. J. Chem. Phys. 2001, 115, 4708-4717.
58. Meyer, S.; Koch, R.; Metzger, J. O. Angew. Chem., Intl. Ed. 2003, 42, 4700-4703.
59. Compare also: Ciminale, F.; Lopez, L.; Paradiso, V.; Nacci, A. Tetrahedron 1996, 52, 13971-13980.