Ab initio studies of the radical cation Diels-Alder reaction

Journal of the American Chemical Society

Volumn 121, Issue 28, 1999, Pages 6730-6736

  Haberl, Udo ^a,b   Wiest, Olaf ^a   Steckhan, Eberhard ^a,b  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; CATION; CYCLOHEXENE DERIVATIVE; ETHYLENE;

ARTICLE; CATALYSIS; ELECTRON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033591942     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983993y     Document Type: Article

References (81)

1. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781.
2. For recent reviews, compare: (a) Borden, W. T.; Lonarich, R. J.; Houk, K. N. Annu. Rev. Phys. Chem. 1988, 39, 213. (b) Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779. (c) Wiest, O.; Montiel, D. C.; Houk, K. N. J. Phys. Chem. A 1997, 101, 8377. (d) Wiest, O.; Houk, K. N. Top. Curr. Chem. 1996, 183, 1.
3. For recent reviews, compare: (a) Borden, W. T.; Lonarich, R. J.; Houk, K. N. Annu. Rev. Phys. Chem. 1988, 39, 213. (b) Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779. (c) Wiest, O.; Montiel, D. C.; Houk, K. N. J. Phys. Chem. A 1997, 101, 8377. (d) Wiest, O.; Houk, K. N. Top. Curr. Chem. 1996, 183, 1.
4. For recent reviews, compare: (a) Borden, W. T.; Lonarich, R. J.; Houk, K. N. Annu. Rev. Phys. Chem. 1988, 39, 213. (b) Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779. (c) Wiest, O.; Montiel, D. C.; Houk, K. N. J. Phys. Chem. A 1997, 101, 8377. (d) Wiest, O.; Houk, K. N. Top. Curr. Chem. 1996, 183, 1.
5. For recent reviews, compare: (a) Borden, W. T.; Lonarich, R. J.; Houk, K. N. Annu. Rev. Phys. Chem. 1988, 39, 213. (b) Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 779. (c) Wiest, O.; Montiel, D. C.; Houk, K. N. J. Phys. Chem. A 1997, 101, 8377. (d) Wiest, O.; Houk, K. N. Top. Curr. Chem. 1996, 183, 1.
6. For recent studies, compare, for example: (a) Beno, B. R.; Houk, K. N.; Singleton, D. A. J. Am. Chem. Soc. 1997, 119, 9984. (b) Karadakov, P. B.; Cooper, D. L.; Gerratt, J. J. Am. Chem. Soc. 1998, 120, 3975.
7. For recent studies, compare, for example: (a) Beno, B. R.; Houk, K. N.; Singleton, D. A. J. Am. Chem. Soc. 1997, 119, 9984. (b) Karadakov, P. B.; Cooper, D. L.; Gerratt, J. J. Am. Chem. Soc. 1998, 120, 3975.
8. (a) Wiest, O.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 901; Angew. Chem. 1993, 105, 932.
9. (a) Wiest, O.; Steckhan, E. Angew. Chem., Int. Ed. Engl. 1993, 32, 901; Angew. Chem. 1993, 105, 932.
10. (b) Wiest, O.; Steckhan, E. Tetrahedron Lett. 1993, 34, 6391.
11. (c) Gieseler, A.; Steckhan, E.; Wiest, O.; Knoch, F.; J. Org. Chem. 1991, 56, 105.
12. (d) Gürtler, C. F.; Steckhan, E.; Blechert, S. J. Org. Chem. 1996, 61, 4136.
13. (e) Peglow, T.; Blechert, S.; Steckhan, E. Chem. Eur. J. 1998, 4, 107.
14. (a) Müller, F.; Mattay, J. Chem. Rev. 1993, 93, 99.
15. (b) Bauld, N. L. Tetrahedron 1989, 45, 5307.
16. (c) Chanon, H.; Eberson, L. Photoinduced Electron-Transfer Reactions; Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, The Netherlands, 1988, p 409.
17. (d) Mattay, J.; Trampe, G.; Runsink, J. Chem. Ber. 1988, 121, 1991.
18. (e) Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, R. A.; Reynolds, D. W.; Wirth, D. D.; Chiou, H. S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371.
19. (a) Harirchian, B.; Bauld, N. L. J. Am. Chem. Soc. 1989, 111, 1826.
20. (b) Gürtler, C. F.; Blechert, S.; Steckhan, E. Angew. Chem., Intl. Ed. Engl. 1995, 34, 1900.
21. (a) Pabon, R. A.; Bellville, D. A.; Bauld, N. L. J. Am. Chem. Soc. 1984, 106, 2730.
22. (b) Reynolds, D. W.; Harirchian, B.; Chiou, H.; Marsh, B. K.; Bauld, N. L. J. Phys. Org. Chem. 1989, 2, 57.
23. (a) Botzem, J.; Haberl, U.; Steckhan, E.; Blechert, S. Acta Chem. Scand. 1998, 52, 175.
24. (b) Pabon, R. A.; Belville, D. J.; Bauld, N. L. J. Am. Chem. Soc. 1984, 106, 2730,
25. (c) Bauld, N. L.; Harirchian, B.; Reynolds, D. W.; Whitem J. C. J. Am. Chem. Soc. 1988, 110, 8111.
26. (a) Lorenz, K. T.; Bauld, N. L. J. Am. Chem. Soc. 1987, 109, 1157.
27. (b) Reynolds, D. W.; Lorenz, K. T.; Chiou, H. S.; Bellville, D. J.; Pabon, R. A.; Bauld, N. L. J. Am. Chem. Soc. 1987, 109, 4960.
28. (c) Gassmann, P. G.; Singleton, D. A. J. Am. Chem. Soc. 1984, 106, 7993.
29. Turecek, F.; Hanus, V. Mass Spectrom. Rev. 1984, 3, 85.
30. (a) Roth, H. D.; Schilling, M. L. M.; Abelt, C. L. Tetrahedron 1986, 42, 6157.
31. (b) Roth, H. D.; Schilling, M. L. J. Am. Chem. Soc. 1985, 107, 716.
32. Bellville, D. J.; Bauld, N. L. Tetrahedron 1986, 42, 6167.
33. (a) Bauld, N. L.; Bellville, D. J.; Pabon, R. A.; Chelsky, R.; Green, G. J. J. Am. Chem. Soc. 1983, 105, 2378.
34. (b) Bellville, D. J.; Bauld, N. L.; Pabon, R. A.; Gardner, S. A. J. Am. Chem. Soc. 1983, 105, 3584.
35. (c) Bauld, N. L. J. Am. Chem. Soc. 1992, 114, 5800.
36. Bellville, D. J.; Bauld, N. L. J. Am. Chem. Soc. 1982, 104, 2665.
37. Mlcoch, J.; Steckhan, E. Tetrahedron Lett. 1987, 27, 1081.
38. Wiest, O.; Steckhan, E.; Grein, F. J. Org. Chem. 1992, 57, 4034.
39. (a) Hrouda, V.; Carsky, P.; Ingr, M.; Chval, Z.; Sastry, G. N.; Bally, T. J. Phys. Chem. A 1998, 102, 9297.
40. (b) Hrouda, V.; Roeselova, M.; Bally T. J. Phys. Chem. A 1997, 101, 3925.
41. (c) Jungwirth, P.; Bally, T. J. Am. Chem. Soc. 1993, 115, 5783.
42. Wiest, O. J. Mol. Struct. (THEOCHEM) 1996, 368, 39.
43. (a) Ma, N. L.; Smith, B. J.; Radom, L. Chem. Phys. Lett. 1992, 193, 386.
44. (b) Nobes, R. H.; Moncrieff, D.; Wong, M. W.; Radom, L.; Gill, P. M. W.; Pople, J. A. Chem. Phys. Lett. 1991, 182, 216.
45. (a) Koga, N.; Morokuma, K. J. J. Am. Chem. Soc. 1991, 113, 1907.
46. (b) Wierschke, S. G.; Nash, J.; Squires, R. R. J. Am. Chem. Soc. 1993, 115, 11958.
47. (c) Lindh, R.; Perrson, B. J. J. Am. Chem. Soc. 1994, 116, 4963.
48. (a) Wang, J.; Becke, A. D.; Smith, V. H., Jr. J. Chem. Phys. 1995, 102, 3477.
49. (b) Laming, G. J.; Handy, N.; Amos, R. D. Mol. Phys. 1993, 80, 1121.
50. (a) Clark, T. Top. Curr. Chem. 1996, 177, 1.
51. (b) Murray, C. W.; Handy, N. C.; J. Chem. Phys. 1992, 97, 6509.
52. (c) Handy, N. C.; Ma, N. L.; Smith, B. J.; Pople, J. A.; Radom, L. J. Am. Chem. Soc. 1991, 113, 7903.
53. (a) Bally, T.; Sastry, G. N. J. Phys. Chem. A 1997, 101, 7923.
54. (b) Braida, B.; Hiberty, P. C.; Savin, A. J. Phys. Chem. A 1998, 102, 7872.
55. (c) Sodupe, N.; Bertran, J.; Rodriguez-Santiago, L.; Baerenz, E. J. J. Phys. Chem. A 1999, 103, 166.
56. MOLDEN Version 3.2 written by G. Schaftenaar (Netherlands). For details of this program, see the URL: http://www.caos.kun.nl/∼schaft/ molden.
57. 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.; l-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; 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.
58. •+ at the B3LYP level is small. An estimate of the BSSE by a counterpoise calculation gave corrections of 0.47 and 0.12 kcal/mol, respectively. At the QCISD(T)// QCISD level, the BSSE is with 2.44 and 7.46 kcal/mol higher.
59. Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036.
60. (a) Wiest, O. J. Am. Chem. Soc. 1997, 119, 5713.
61. (b) Sastry G. N.; Bally, T.; Hrouda, V.; Carsky, P. J. Am. Chem. Soc. 1998, 120, 9323.
62. Bischoff, P. J. J. Am. Chem. Soc. 1977, 99, 8145.
63. Beno, B.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 4816.
64. It has for, example, been shown that the [2 + 2] cycloreversion of the cyclobutane radical cation proceeds in a supra-suprafacial manner (compare ref 17c).
65. Williams, F. J. Chem. Soc., Faraday Trans. 1994, 90, 1681.
66. (a) Osamura, K.; Kato, S.; Morokuma, K.; Feller, D.; Davidson, E. R.; Borden, W. T. J. Am. Chem. Soc. 1984, 106, 3362.
67. (b) Dupuis, M.; Murray, C.; Davidson, E. R. J. Am. Chem. Soc. 1991, 113, 9756.
68. For recent examples, compare, for example: (a) Doubleday, C.; Bolton, K.; Hase, W. L. J. Phys. Chem. A 1998, 102, 3648. (b) Carpenter, B. K. J. Am. Chem. Soc. 1995, 117, 6336. (c) Carpenter, B. K. Am. Sci. 1997, 85, 138.
69. For recent examples, compare, for example: (a) Doubleday, C.; Bolton, K.; Hase, W. L. J. Phys. Chem. A 1998, 102, 3648. (b) Carpenter, B. K. J. Am. Chem. Soc. 1995, 117, 6336. (c) Carpenter, B. K. Am. Sci. 1997, 85, 138.
70. For recent examples, compare, for example: (a) Doubleday, C.; Bolton, K.; Hase, W. L. J. Phys. Chem. A 1998, 102, 3648. (b) Carpenter, B. K. J. Am. Chem. Soc. 1995, 117, 6336. (c) Carpenter, B. K. Am. Sci. 1997, 85, 138.
71. (a) Swenton, J. S.; Bartlett, P. D. J. Am. Chem. Soc. 1968, 90, 2056.
72. (b) Klärner, F.-G.; Krawczyk, B.; Ruster, V.; Deiters, U. K. J. Am. Chem. Soc. 1994, 116, 7646.
73. f (cyclohexene) = -1.03 ± 0.23 kcal/mol, IE (cyclohexene) = 8.945 ± 0.010 eV. (a) Prosen, E. J.; Maron, F. W.; Rossini, F. D. J. Res. Natl. Bur. Stand. (U.S.) 1951, 46, 106. (b) Chase, M. W., Jr. J. Phys. Chem. Ref. Data, Monograph 9, 1998, 1. (c) Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K.; Tasker, I. R. J. Chem. Eng. Data, 1996, 41, 1269.
74. f (cyclohexene) = -1.03 ± 0.23 kcal/mol, IE (cyclohexene) = 8.945 ± 0.010 eV. (a) Prosen, E. J.; Maron, F. W.; Rossini, F. D. J. Res. Natl. Bur. Stand. (U.S.) 1951, 46, 106. (b) Chase, M. W., Jr. J. Phys. Chem. Ref. Data, Monograph 9, 1998, 1. (c) Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K.; Tasker, I. R. J. Chem. Eng. Data, 1996, 41, 1269.
75. f (cyclohexene) = -1.03 ± 0.23 kcal/mol, IE (cyclohexene) = 8.945 ± 0.010 eV. (a) Prosen, E. J.; Maron, F. W.; Rossini, F. D. J. Res. Natl. Bur. Stand. (U.S.) 1951, 46, 106. (b) Chase, M. W., Jr. J. Phys. Chem. Ref. Data, Monograph 9, 1998, 1. (c) Steele, W. V.; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K.; Tasker, I. R. J. Chem. Eng. Data, 1996, 41, 1269.
76. (d) Lias, S. D.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. Ion Energetics Data. In NIST Chemistry WebBook; Mallard, W. G., Linstrom, P. J., Eds.; NIST Standard Reference Database Number 69, November 1998, National Institute of Standards and Technology, Gaithersburg MD, 20899 (http://webbook.nist-.gov).
77. Haberl, U.; Steckhan, E.; Blechert, S.; Wiest, O. Chem. Eur. J., in press.
78. •+ to 10.
79. For a detailed discussion, compare: Bally, T.; Borden, W. T. In Reviews in Computational Chemistry, Lipkowitz, K. B., Boyd, D. B., Eds.; VCH-Wiley: New York, 1999; Vol. 13.
80. Barone, V.; Rega, N.; Bally, T. J. Phys. Chem A 1999, 103, 217.
81. Swinarski, D. J.; Wiest, O., to be submitted for publication.