Aromaticity of pericyclic reaction transition structures: Magnetic evidence

Journal of Physical Organic Chemistry

Volumn 11, Issue 8-9, 1998, Pages 655-662

  Jiao, Haijun ^a   Von Schleyer, Paul Ragué ^a,b  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

Aromaticity; Magnetic susceptibility; Pericyclic reaction transition structures

Indexed keywords

EID: 11644271412     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-1395(199808/09)11:8/9<655::aid-poc66>3.0.co;2-u     Document Type: Article

References (68)

1. M. G. Evans and E. Warhurst. Trans. Faraday Soc. 34, 614 (1938).
2. M. G. Evans. Trans. Faraday Soc. 35, 824 (1939).
3. R. B. Woodward and R. Hoffmann. The Conservation of Orbital Symmetry. Verlag Chemie, Weinheim (1970).
4. H. Zimmerman. Acc. Chem. Res. 33, 272 (1971).
5. . For a review see M. J. S. Dewar. Angew. Chem., Int. Ed. Engl. 10, 761 (1971), and references cited therein.
6. M. J. S. Dewar and C. Jie. Acc. Chem. Res. 25, 537 (1992), and references cited therein.
7. . For review see (a) K. N. Houk, Y. Li and J. D. Evanseck. Angew. Chem., Int. Ed. Eng. 31, 682 (1992); (b) K. N. Houk, J. Gonzalez and Y. Li. Acc. Chem. Res. 28, 81 (1995); (c) W. T. Borden. Acc. Chem. Res. 29, (1996); (d) W. R. Dolbier, Jr, H. Koroniak, K. N. Houk and C. Sheu. Acc. Chem. Res. 29, 471 (1996); (e) J. J. Gajewski. Acc. Chem. Res. 30, 219 (1997); (f) J. Bertran, V. Branchadell, A. Oliva and M. Sodupe. Acc. Chem. Res. in press.
8. . For review see (a) K. N. Houk, Y. Li and J. D. Evanseck. Angew. Chem., Int. Ed. Eng. 31, 682 (1992); (b) K. N. Houk, J. Gonzalez and Y. Li. Acc. Chem. Res. 28, 81 (1995); (c) W. T. Borden. Acc. Chem. Res. 29, (1996); (d) W. R. Dolbier, Jr, H. Koroniak, K. N. Houk and C. Sheu. Acc. Chem. Res. 29, 471 (1996); (e) J. J. Gajewski. Acc. Chem. Res. 30, 219 (1997); (f) J. Bertran, V. Branchadell, A. Oliva and M. Sodupe. Acc. Chem. Res. in press.
9. . For review see (a) K. N. Houk, Y. Li and J. D. Evanseck. Angew. Chem., Int. Ed. Eng. 31, 682 (1992); (b) K. N. Houk, J. Gonzalez and Y. Li. Acc. Chem. Res. 28, 81 (1995); (c) W. T. Borden. Acc. Chem. Res. 29, (1996); (d) W. R. Dolbier, Jr, H. Koroniak, K. N. Houk and C. Sheu. Acc. Chem. Res. 29, 471 (1996); (e) J. J. Gajewski. Acc. Chem. Res. 30, 219 (1997); (f) J. Bertran, V. Branchadell, A. Oliva and M. Sodupe. Acc. Chem. Res. in press.
10. . For review see (a) K. N. Houk, Y. Li and J. D. Evanseck. Angew. Chem., Int. Ed. Eng. 31, 682 (1992); (b) K. N. Houk, J. Gonzalez and Y. Li. Acc. Chem. Res. 28, 81 (1995); (c) W. T. Borden. Acc. Chem. Res. 29, (1996); (d) W. R. Dolbier, Jr, H. Koroniak, K. N. Houk and C. Sheu. Acc. Chem. Res. 29, 471 (1996); (e) J. J. Gajewski. Acc. Chem. Res. 30, 219 (1997); (f) J. Bertran, V. Branchadell, A. Oliva and M. Sodupe. Acc. Chem. Res. in press.
11. . For review see (a) K. N. Houk, Y. Li and J. D. Evanseck. Angew. Chem., Int. Ed. Eng. 31, 682 (1992); (b) K. N. Houk, J. Gonzalez and Y. Li. Acc. Chem. Res. 28, 81 (1995); (c) W. T. Borden. Acc. Chem. Res. 29, (1996); (d) W. R. Dolbier, Jr, H. Koroniak, K. N. Houk and C. Sheu. Acc. Chem. Res. 29, 471 (1996); (e) J. J. Gajewski. Acc. Chem. Res. 30, 219 (1997); (f) J. Bertran, V. Branchadell, A. Oliva and M. Sodupe. Acc. Chem. Res. in press.
12. . For review see (a) K. N. Houk, Y. Li and J. D. Evanseck. Angew. Chem., Int. Ed. Eng. 31, 682 (1992); (b) K. N. Houk, J. Gonzalez and Y. Li. Acc. Chem. Res. 28, 81 (1995); (c) W. T. Borden. Acc. Chem. Res. 29, (1996); (d) W. R. Dolbier, Jr, H. Koroniak, K. N. Houk and C. Sheu. Acc. Chem. Res. 29, 471 (1996); (e) J. J. Gajewski. Acc. Chem. Res. 30, 219 (1997); (f) J. Bertran, V. Branchadell, A. Oliva and M. Sodupe. Acc. Chem. Res. in press.
13. (a) H. Jiao and P. v. R. Schleyer. Angew. Chem., Int. Ed. Engl. 32, 1763 (1993);
14. (b) H. Jiao and P. v. R. Schleyer. J. Chem. Soc., Perkin Trans. 2 407 (1994);
15. (c) R. Herges, H. Jiao and P. v. R. Schleyer. Angew. Chem., Int. Ed. Engl. 33, 1376 (1994);
16. (d) H. Jiao and P. v. R. Schleyer. J. Chem. Soc., Faraday Trans. 90, 1559 (1994);
17. (e) H. Jiao and P. v. R. Schleyer. J. Am. Chem. Soc. 117, 11529 (1995);
18. (f) H. Jiao and P. v. R. Schleyer. Angew. Chem., Int. Ed. Engl. 34, 334 (1994).
19. For a review see O. Wiest and K. N. Houk. Top. Curr. Chem. 182, 1 (1996).
20. W. v. E. Doering, W. R. Roth, R. Breuckman, L. Figge, H.-W. Lenartz, W. D. Fessner and H. Prinzbach. Chem. Ber. 121, 1 (1988).
21. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao and N. J. v. E. Hommes. J. Am. Chem. Soc. 118, 6317 (1996).
22. (a) H. Jiao and P. v. R. Schleyer. Angew. Chem., Int. Ed. Engl. 35, 2383 (1996);
23. (b) G. Subramanian, P. v. R. Schleyer and H. Jiao. Angew. Chem., Int. Ed. Engl. 35 2638 (1996);
24. (c) G. Subramanian, P. v. R. Schleyer and H. Jiao. Organometallics 16, 2362 (1997);
25. (d) H. Jiao, P. v. R. Schleyer, Y. Mo, M. A. McAllister and T. T. Tidwell. J. Am. Chem. Soc. 119, 6561 (1997).
26. B. Lecea, I. Morao and F. Cossio. J. Org. Chem. 62, 7033 (1997).
27. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople. Gaussian 94, Revision D.3. Gaussian, Pittsburgh, PA (1995).
28. (a) W. Kutzelnigg, M. Schindler and Fleischer. NMR, Basic Principles and Progress. Springer, Berlin (1990);
29. (b) M. Schindler and W. Kutzelnigg. J. Chem. Phys. 76, 1919 (1982).
30. J. Pipek and P. G. Mezey. J. Chem. Phys. 90, 4916 (1989); for applications, see P. v. R. Schleyer, H. Jiao, N. J. R. van E. Hommes, V. G. Malkin and O. L. Markin. J. Am. Chem. Soc. 119, 12669 (1997).
31. J. Pipek and P. G. Mezey. J. Chem. Phys. 90, 4916 (1989); for applications, see P. v. R. Schleyer, H. Jiao, N. J. R. van E. Hommes, V. G. Malkin and O. L. Markin. J. Am. Chem. Soc. 119, 12669 (1997).
32. (a) V. G. Malkin, O. L. Malkin, L. A. Eriksson and D. R. Salahub. in Modern Density Functional Theory, edited by J. M. Seminario and P. Politzer, p. 273, and references cited therein. Elsevier, Amsterdam (1995),
33. (b) V. G. Malkin, O. L. Malkin, L. A. Eriksson and D. R. Salahub. J. Am. Chem. Soc. 116, 5898 (1994).
34. K. N. Houk, R. W. Gandour, R. W. Strozier, N. G. Rondan and L. A. Paquette. J. Am. Chem. Soc. 101, 6797 (1979).
35. R. D. Bach, G. J. Wolber and H. B. Schlegel. J. Am. Chem. Soc. 107, 2837 (1985).
36. (a) H. P. Dauben, Jr, J. D. Wilson and J. L. Laity. J. Am. Chem. Soc. 90, 811 (1968);
37. (b) H. P. Dauben, J. D. Wilson, Jr and J. L. Laity. J. Am. Chem. Soc. 91, 1991 (1969);
38. (c) H. P. Dauben, Jr, J. D. Wilson and J. L. Laity. in Nonbenzenoid Aromatics, edited by Synder, Vol. II. Academic Press, New York (1971).
39. P. v. R. Schleyer and H. Jiao. Pure Appl. Chem. 68, 209 (1996);
40. (b) P. v. R. Schleyer, P. Freeman, H. Jiao and B. Goldfuss. Angew. Chem., Int. Ed. Engl. 34, 337 (1995);
41. (c) H. M. Sulzbach, P. v. R. Schleyer, H. Jiao, Y. Xie and H. F. Schaefer III. J. Am. Chem. Soc. 117, 1367 (1995);
42. (d) P. v. R. Schleyer, H. Jiao, M. H. Sulzbach and H. F. Schaefer III. J. Am. Chem. Soc. 118, 2093 (1996);
43. (e) H. Jiao, N. J. R. van E. Hommes, P. v. R. Schleyer and A. de Meijere. J. Org. Chem. 61, 2828 (1996);
44. (f) T. Zywietz, H. Jiao, P. v. R. Schleyer and A. de Meijere, J. Org. Chem., 63, 3417 (1998);
45. (g) M. Nendel, K. N. Houk, L. M. Tolbert, E. Vogel, H. Jiao and P. v. R. Schleyer, J. Phys. Chem. (1998) in press.
46. R. B. Woodward, T. Fukunaga and R. C. Kelly. J. Am. Chem. Soc. 86, 3162 (1964).
47. E. D. Stevens, J. D. Kramer and L. A. Paquette. J. Org. Chem. 41, 2267 (1976).
48. (a) J. F. Liebman, L. A. Paquette, J. R. Peterson and D. W. Rogers. J. Am. Chem. Soc. 108, 8267 (1986);
49. (b) D. W. Rogers, S. A. Loggins, D. D. Samuel and M. A. Finnerty. Struct. Chem. 1, 481 (1990).
50. (a) M. A. Miller, J. M. Schulman and R. L. Disch. J. Am. Chem. Soc. 110, 7681 (1988);
51. (b) M. J. S. Dewar and A. J. Holder. J. Am. Chem. Soc. 111, 5384 (1989);
52. (c) J. W. Storer and K. N. Houk. J. Am. Chem. Soc. 114, 1165 (1992);
53. (d) S. P. Verevkin, H.-D. Beckhaus, C. Rückhardt, R. Haag, S. I. Kozhushkov, T. Zywietz, A. de Meijere, H. Jiao and P. v. R. Schleyer, J. Am. Chem. Soc. (1998) in press.
54. 2), -11.5 (>CH-), -7.6 (>C<), -10.0 (-CH=), -6.9 (>C=) and -19.0 (cisA -HC=CH-).
55. A. de Meijere, D. Kaufmann and O. Schallner, Tetrahedron Lett. 553 (1973).
56. H. Jiao, P. v. R. Schleyer and M. N. Glukhovtsev. J. Phys. Chem. 100, 12299 (1996), and references cited therein.
57. (a) F. Bernardi, A. Bottoni, M. J. Field, M. F. Guest, I. H. Hillier, M. A. Robb and A. Venturini. J. Am. Chem. Soc. 110, 7478 (1988);
58. (b) Y. Li and K. N. Houk. J. Am. Chem. Soc. 115, 7478 (1993);
59. (c) E. Goldstein, B. Beno and K. N. Houk. J. Am. Chem. Soc. 118, 6036 (1996);
60. (d) B. Beno, K. N. Houk and D. A. Singleton. J. Am. Chem. Soc. 118, 9984 (1996).
61. F. Jensen and K. N. Houk. J. Am. Chem. Soc. 109, 3139 (1987), and references cited therein.
62. D. A. Hrovat, K. Morokuma and W. T. Borden. J. Am. Chem. Soc. 116, 1072 (1994).
63. W. v. E. Doering, V. G. Toscano and G. H. Beasley. Tetrahedron, 27, 5299 (1971).
64. W. R. Roth, H.-W. Lenartz, W. v. E. Doering, L. Birladeanu, C. Guyton and T. Kitagawa. J. Am. Chem. Soc. 112, 1722 (1990).
65. (a) O. Wiest, K. A. Black and K. N. Houk. J. Am. Chem. Soc. 116, 10336 (1994);
66. (b) H. Y. Yoo and K. N. Houk. J. Am. Chem. Soc. 116, 12047 (1994), and references cited therein.
67. O. Wiest, K. N. Houk, K. A. Black and B. Thomas IV. J. Am. Chem. Soc. 117, 8594 (1995).
68. D. C. Spellmeyer and K. N. Houk. J. Am. Chem. Soc. 110, 3412 (1988), and references cited therein.