Isotope effects on the ring inversion of cyclooctatetraene

Journal of the American Chemical Society

Volumn 120, Issue 34, 1998, Pages 8864-8867

  Stevenson, Cheryl D ^a   Brown, Eric C ^a   Hrovat, David A ^b   Borden, Weston Thatcher ^b  

^a ILLINOIS STATE UNIVERSITY   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANNULENE DERIVATIVE; BENZENE; ISOTOPE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; TEMPERATURE;

EID: 0032475401     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981496b     Document Type: Article

References (44)

1. Reviews: (a) Schröder, G. Cyclooctatetraene; Verlag Chemie GmbH: Weinheim, 1965. (b) Paquette, L. A. Tetrahedron 1975, 31, 2855-2883. (c) Fray, G. I.; Saxton, R. G. The Chemistry of Cyclooctatetraene and Its Derivatives; Cambridge University Press: New York, 1978. (d) Paquette, L. A. Pure Appl. Chem. 1982, 54, 987-1004 1982. (e) Paquette, L. A. Acc. Chem. Res. 1992, 26, 57-62. (f) Paquette, L. A. In Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1992; Vol. 2, pp 1-77.
2. Reviews: (a) Schröder, G. Cyclooctatetraene; Verlag Chemie GmbH: Weinheim, 1965. (b) Paquette, L. A. Tetrahedron 1975, 31, 2855-2883. (c) Fray, G. I.; Saxton, R. G. The Chemistry of Cyclooctatetraene and Its Derivatives; Cambridge University Press: New York, 1978. (d) Paquette, L. A. Pure Appl. Chem. 1982, 54, 987-1004 1982. (e) Paquette, L. A. Acc. Chem. Res. 1992, 26, 57-62. (f) Paquette, L. A. In Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1992; Vol. 2, pp 1-77.
3. Reviews: (a) Schröder, G. Cyclooctatetraene; Verlag Chemie GmbH: Weinheim, 1965. (b) Paquette, L. A. Tetrahedron 1975, 31, 2855-2883. (c) Fray, G. I.; Saxton, R. G. The Chemistry of Cyclooctatetraene and Its Derivatives; Cambridge University Press: New York, 1978. (d) Paquette, L. A. Pure Appl. Chem. 1982, 54, 987-1004 1982. (e) Paquette, L. A. Acc. Chem. Res. 1992, 26, 57-62. (f) Paquette, L. A. In Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1992; Vol. 2, pp 1-77.
4. Reviews: (a) Schröder, G. Cyclooctatetraene; Verlag Chemie GmbH: Weinheim, 1965. (b) Paquette, L. A. Tetrahedron 1975, 31, 2855-2883. (c) Fray, G. I.; Saxton, R. G. The Chemistry of Cyclooctatetraene and Its Derivatives; Cambridge University Press: New York, 1978. (d) Paquette, L. A. Pure Appl. Chem. 1982, 54, 987-1004 1982. (e) Paquette, L. A. Acc. Chem. Res. 1992, 26, 57-62. (f) Paquette, L. A. In Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1992; Vol. 2, pp 1-77.
5. Reviews: (a) Schröder, G. Cyclooctatetraene; Verlag Chemie GmbH: Weinheim, 1965. (b) Paquette, L. A. Tetrahedron 1975, 31, 2855-2883. (c) Fray, G. I.; Saxton, R. G. The Chemistry of Cyclooctatetraene and Its Derivatives; Cambridge University Press: New York, 1978. (d) Paquette, L. A. Pure Appl. Chem. 1982, 54, 987-1004 1982. (e) Paquette, L. A. Acc. Chem. Res. 1992, 26, 57-62. (f) Paquette, L. A. In Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1992; Vol. 2, pp 1-77.
6. Reviews: (a) Schröder, G. Cyclooctatetraene; Verlag Chemie GmbH: Weinheim, 1965. (b) Paquette, L. A. Tetrahedron 1975, 31, 2855-2883. (c) Fray, G. I.; Saxton, R. G. The Chemistry of Cyclooctatetraene and Its Derivatives; Cambridge University Press: New York, 1978. (d) Paquette, L. A. Pure Appl. Chem. 1982, 54, 987-1004 1982. (e) Paquette, L. A. Acc. Chem. Res. 1992, 26, 57-62. (f) Paquette, L. A. In Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1992; Vol. 2, pp 1-77.
7. Anet, F. A. L.; Bourn, A. J. R.; Lin, Y. S. J. Am. Chem. Soc. 1964, 86, 3576.
8. Oth, J. F. M. Pure Apple. Chem. 1971, 25, 573.
9. (a) Anet, F. A. L. J. Am. Chem. Soc. 1962, 84, 671.
10. (b) Naor, R.; Luz, Z. J. Chem. Phys. 1982, 76, 5662.
11. (c) Gwynn, D. E.; Whitesides, G. M.; Roberts, J. D. J. Am. Chem. Soc. 1965, 87, 2862.
12. (a) Paquette, L. A.; Trova, M. P.; Luo, J.; Clough, A. E.; Anderson, L. B. J. Am. Chem. Soc., 1990, 112, 228.
13. (b) Paquette, L. A.; Wang, T.-Z.; Luo, J.; Cottrell, C. E.; Clough, A. E.; Anderson, L. B. J. Am. Chem. Soc. 1990, 112, 239 and references therein,
14. (c) Ermer, O.; Klärner, F.-G.; Wette, M. J. Am. Chem. Soc. 1986, 108, 4908.
15. Wenthold, P. G.; Hrovat, D. A.; Borden, W. T.; Lineberger, W. C. Science 1996, 272, 1456.
16. Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1992, 114, 5879.
17. 6.
18. Hammons, J. H.; Hrovat, D. A.; Borden, W. T. J. Am. Chem. Soc. 1991, 113, 4500.
19. (a) Katz, T. J.; Strauss, H. L. J. Chem. Phys. 1960, 32, 1873.
20. (b) Blankenspoor, R. L.; Snavely, C. M. J. Org. Chem. 1976, 41, 2071.
21. (c) Bauld, N. L.; Farr, F. R.; Hudson, C. E. J. Am. Chem. Soc. 1974, 96, 5634.
22. (d) Hammons, J. H.; Kresge, C. T.; Paquette, L. A. J. Am. Chem. Soc. 1976, 98, 8172.
23. (e) Katz, T. J. J. Am. Chem. Soc. 1960, 82, 3785.
24. (f) Strauss, H. L.; Katz, T. J.; Fraenkel, G. K. J. Am. Chem. Soc. 1963, 85, 2360.
25. (g) Kimmel, P. I.; Strauss, H. L. J. Phys. Chem. 1968, 72, 2813.
26. (h) Allendoerfer, R. D.; Rieger, P. H. J. Am. Chem. Soc. 1965, 87, 2336.
27. Hrovat, D. A.; Hammons, J. H.; Stevenson, C. D.; Borden, W. T. J. Am. Chem. Soc. 1997, 119, 9523.
28. Stevenson, C. D.; Peters, S. J.; Reidy, K. A.; Reiter, R. C. J. Org. Chem. 1992, 57, 1877.
29. (a) Stevenson, C. D.; Espe, M. P.; Reiter, R. C. J. Am. Chem. Soc. 1986, 108, 533.
30. (b) Stevenson, C. D.; Espe, M. P.; Reiter, R. C. J. Am. Chem. Soc. 1986, 108, 5760.
31. (c) Lauricella, T. L.; Pescatore, J. A.; Reiter, R. C.; Stevenson, R. D.; Stevenson, C. D. J. Phys. Chem. 1988, 92, 3687.
32. (d) Stevenson, C. D.; Sturgeon, B. E.; Vines, S. K.; Peters, S. J. J. Phys. Chem. 1988, 92, 6850.
33. (e) Stevenson, C. D.; Reidy, K. A.; Peters, S. J.; Reiter, R. C. J. Am. Chem. Soc. 1989, 111, 6578.
34. (f) Stevenson, C. D.; Sturgeon, J. Org. Chem. 1990, 55, 4090.
35. (g) Stevenson, C. D.; Halvorsen T. D.; Reiter, R. C. J. Am. Chem. Soc. 1993, 115, 12405.
36. PM3 calculations failed to reproduce these trends: Zuilhof, H.; Lodder, G. J. Phys. Chem. 1995, 99, 8033.
37. (a) Bigeleisen, J.; Mayer, M. G. J. Chem. Phys. 1947, 15, 261.
38. (b) Wolfsberg, M. Acc. Chem. Res. 1972, 5, 225.
39. Reppe, W.; Schlichting, O.; Klager, K.; Toepel, T. Annalen 1948, 560, 1.
40. (a) Stevenson, C. D.; Burton, R. D.; Reiter, R. C. J. Am. Chem. Soc. 1992, 114, 399.
41. (b) Stevenson, C. D.; Burton, R. D.; Reiter, R. C. J. Am. Chem. Soc. 1992, 114, 4514.
42. Krebs, A. Angew. Chem. 1965, 77, 1966.
43. van Geet, A. L. Anal. Chem. 1968, 40, 2227.
44. gNMR, v. 4.0, Cherwell Scientific Publishing Limited, Oxford, UK, 1997.