Rate constants for 1,2-hydrogen migration in cyclohexylidene and in substituted cyclohexylidenes

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4456-4464

  Pezacki, John Paul ^a   Couture, Philippe ^a   Dunn, James A ^a   Warkentin, John ^a   Wood, Paul D ^b   Lusztyk, Janusz ^b   Ford, Francis ^c   Platz, Matthew S ^c  

^a MCMASTER UNIVERSITY   (Canada)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^c OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE; CYCLOHEXENE DERIVATIVE; CYCLOHEXYLIDENE DERIVATIVE; HYDROGEN; OXADIAZOLE DERIVATIVE; PYRIDINE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; IRRADIATION; PHOTOLYSIS; REACTION ANALYSIS; STEADY STATE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0033546266     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990171q     Document Type: Article

References (69)

1. Issued as NRCC No. 42177.
2. For reviews, see: (a) Moss, R. A. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, 1994; Vol. 1, p 59. (b) Jackson, J. E.; Platz, M. S. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, 1994; Vol. 1, p 89.
3. For reviews, see: (a) Moss, R. A. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, 1994; Vol. 1, p 59. (b) Jackson, J. E.; Platz, M. S. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, 1994; Vol. 1, p 89.
4. (a) Jackson, J. E.; Soundararajan, N.; Platz, M. S.; Doyle, M. P.; Liu, M. T. H. Tetrahedron Lett. 1989, 30, 1335.
5. (b) Jackson, J. E.; Soundararajan, N.; Platz, M. S.; Liu, M. T. H. J. Am. Chem. Soc. 1988, 110, 5595.
6. (c) Platz, M. S.; Modarelli, D.; Morgan, S.; White, W. R.; Mullins, M.; Celebi, S.; Toscano, J. P. Progress of Reaction Kinetics; Rodgers, M. A., Ed.; Elsevier: 1994; Vol. 19, p 93.
7. (a) Modarelli, D. A.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 8985.
8. (b) Morgan, S.; Jackson, J. E.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 2782.
9. (c) Modarelli, D. A.; Morgan, S.; Platz, M. S. J. Am. Chem. Soc. 1992, 114, 7034.
10. (d) Ford, F.; Yuzawa, T.; Platz, M. S.; Matzinger, S.; Fülscher, M. J. Am. Chem. Soc. 1998, 120, 4430.
11. (a) Bonneau, R.; Liu, M. T. H.; Rayez, M. T. J. Am. Chem. Soc. 1989, 111, 5973.
12. (b) Liu, M. T. H.; Bonneau, R. J. Am. Chem. Soc. 1989, 111, 6873.
13. (c) LaVilla, J. A.; Goodman, J. L. J. Am. Chem. Soc. 1989, 111, 6877.
14. LaVilla, J. A.; Goodman, J. L. Tetrahedron Lett. 1990, 31, 5109.
15. Sheridan, R. S.; Moss, R. A.; Wilk, B. K.; Shen, S.; Włostowski, M.; Kesselmayer, M. A.; Subramanian, R.; Kmiecik-Lawrynowicz, G.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1988, 110, 7563.
16. Sugiyama, M. H.; Celebi, S.; Platz, M. S. J. Am. Chem. Soc. 1992, 114, 966.
17. Moss, R. A.; Yan, S.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1998, 120, 1088.
18. (a) Kenar, J. A.; Nickon, A. Tetrahedron 1997, 53, 14871.
19. (b) Nickon, A. Acc. Chem. Res. 1993, 26, 84.
20. (c) Kenar, J. A.; Nickon, A. Tetrahedron Lett. 1994, 35, 9657.
21. (d) Evanseck, J. D.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 9148.
22. (a) Nickon, A.; Stern, A. G.; Ilao, M. C. Tetrahedron Lett. 1993, 34, 1391.
23. (b) Stern, A. G.; Ilao, M. C.; Nickon, A. Tetrahedron 1993, 49, 8107.
24. Kyba, E. P.; John, A. M. J. Am. Chem. Soc. 1977, 99, 8329.
25. Seghers, L.; Schechter, H. Tetrahedron Lett. 1976, 1943.
26. Press, L. S.; Schechter, H. J. Am. Chem. Soc. 1979, 101, 509.
27. Unpublished results by the Platz group.
28. For discussions and leading references, see: (a) Moss, R. A. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, 1994; Vol. 1, p 59. (b) Moss, R. A. Pure Appl. Chem. 1995, 67, 741. (c) Platz, M. S.; White, W. R., III; Modarelli, D. A.; Celebi, S. Res. Chem. Intermed. 1994, 20, 175.
29. For discussions and leading references, see: (a) Moss, R. A. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, 1994; Vol. 1, p 59. (b) Moss, R. A. Pure Appl. Chem. 1995, 67, 741. (c) Platz, M. S.; White, W. R., III; Modarelli, D. A.; Celebi, S. Res. Chem. Intermed. 1994, 20, 175.
30. For discussions and leading references, see: (a) Moss, R. A. In Advances in Carbene Chemistry; Brinker, U., Ed.; JAI Press: Greenwich, 1994; Vol. 1, p 59. (b) Moss, R. A. Pure Appl. Chem. 1995, 67, 741. (c) Platz, M. S.; White, W. R., III; Modarelli, D. A.; Celebi, S. Res. Chem. Intermed. 1994, 20, 175.
31. Pezacki, J. P.; Pole, D. L.; Warkentin, J.; Chen, T.; Ford, F.; Toscano, J.; Fell, J.; Platz, M. S. J. Am. Chem. Soc. 1997, 119, 3191.
32. El-Saidi, M.; Kassam, K.; Pole, D. L.; Tadey, T.; Warkentin, J. J. Am. Chem. Soc. 1992, 114, 8751 and references therein.
33. Cantacuzène, D.; Wakselman, C.; Dorme, R. J. Chem. Soc., Perkin Trans. 1 1977, 1365.
34. (a) Pezacki, J. P.; Wagner, B. D.; Lew, C. S. Q.; Warkentin, J.; Lusztyk, J. J. Am. Chem. Soc. 1997, 119, 1789.
35. (b) Majchrzak, M. W.; Békhazi, M.; Tse-Sheepy, I.; Warkentin, J. J. Org. Chem. 1989, 54, 1842.
36. (c) Majchrzak, M. W.; Jefferson, E. A.; Warkentin, J. J. Am. Chem. Soc. 1990, 112, 1842.
37. (d) Jefferson, E. A.; Warkentin, J. J. Org. Chem. 1994, 59, 455.
38. (e) Adam, W.; Finzel, R. Tetrahedron Lett. 1990, 31, 863.
39. (a) Kassam, K.; Warkentin, J. Can. J. Chem. 1997, 75, 120.
40. (b) Win, W. W.; Kao, M.; Eiermann, M.; McNamara, J. J., Wudl, F., Pole, D. L.; Kassam, K.; Warkentin, J. J. Org. Chem. 1994, 59, 5871.
41. (c) Kassam, K.; Warkentin, J. J. Org. Chem. 1994, 59, 5071-5.
42. (d) Isaacs, L.; Diederich, F. Helv. Chim. Acta 1993, 76, 2454-64.
43. (e) El-Saidi, M.; Kassam, K.; Pole, D. L.; Tadey, T.; Warkentin, J. J. Am. Chem. Soc. 1992, 114, 8751-2.
44. (f) Rigby, J. H.; Cavezza, A.; Ahmed, G. J. Am. Chem. Soc. 1996, 118, 12848.
45. (g) Rigby, J. H.; Cavezza, A.; Heeg, M. J. J. Am. Chem. Soc. 1998, 120, 3664.
46. (a) Pezacki, J. P.; Wood, P. D.; Gadosy, T. A.; Lusztyk, J.; Warkentin, J. J. Am. Chem. Soc. 1998, 120, 8681.
47. (b) Pezacki, J. P.; Warkentin, J.; Wood, P. D.; Lusztyk, J., Yuzawa, T.; Gudmundsdottir, A. D.; Morgan, S.; Platz, M. S. J. Photochem. Photobiol. A Chem. 1998, 116, 1.
48. Moss, R. A.; Włostowski, M.; Shen, S.; Krogh-Jespersen, K.; Matro, A. J. Am. Chem. Soc. 1988, 110, 4443.
49. 2 complexation and release to obtain solutions of pyridine which did not absorb light at 308 nm, see: Heap, J.; Jones, W. J.; Speakman, J. B. J. Am. Chem. Soc. 1921, 43, 1936. Very pure pyridine turns yellow over a period of 10-30 min at room temperature when exposed to oxygen.
50. The major problem with the linearized functions is that they give excessive weighting to points which may be poorly defined.
51. (a) Matzinger, S.; Fülscher, M. P. J. Phys. Chem. 1995, 99, 10747.
52. (b) Richards, C. A., Jr.; Kim, S.-J.; Yamaguchi, Y.; Schaefer, H. F., III. J. Am. Chem. Soc. 1995, 117, 10104.
53. (c) Sulzbach, H. M.; Bolton, E.; Lenoir, D.; Schleyer, P. v. R.; Schaefer, H. F., III. J. Am. Chem. Soc. 1996, 118, 9908.
54. (a) Morgan, S.; Jackson, J. E.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 2782.
55. (b) Bally, T.; Matzinger, S.; Truttman, C.; Platz, M. S.; Morgan, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 1964.
56. t → triplet derived products
57. Ge, C. S.; Jang, E. G.; Jefferson, E. A.; Liu, W.; Moss, R. A.; Wostowska, J.; Xue, S. J. Chem. Soc., Chem. Commun. 1994, 1479.
58. We prefer not to draw a virtual (unreal) p orbital, to which migration formally occurs, at the carbene carbon.
59. Oki, M. Applications of Dynamic NMR Spectroscopy to Organic Chemistry. In Methods of Stereochemical Analysis; Marchand, A. P., Ed.; Vol. 4, VCH: Deerfield Beach, FL, 1985; pp 297-298.
60. Mansoor, A. M.; Stevens, I. D. R. Tetrahedron Lett. 1966, 1733.
61. Sulzbach, H. M.; Platz, M. S.; Schaefer, H. F., III; Hadad, C. M. J. Am. Chem. Soc. 1997, 119, 5682.
62. Seghers, L.; Shechter, H. Tetrahedron Lett. 1976, 1943.
63. Press, L. S.; Shechter, H. J. Am. Chem. Soc. 1979, 101, 509.
64. (a) Haas, A.; Plümer, R.; Schiller, A. Chem. Ber. 1985, 118, 3004.
65. (b) Bouillon, J.-P.; Maliverny, C.; Merènyi, R.; Viehe, H. G. J. Chem. Soc., Perkin Trans. 1 1991, 2147.
66. Abelt, C. J.; Pleier, J. M. J. Am. Chem, Soc, 1989, 111, 1795.
67. Okimoto, M.; Chiba, T. J. Org. Chem. 1990, 55, 1070.
68. Kazanis, S.; Azarani, A.; Johnston, L. J. J. Phys. Chem. 1991, 95, 4430.
69. Gritsan, N. P.; Zhai, H. B.; Yuzawa, T.; Brooke, J.; Platz, M. S. J. Phys. Chem. A 1997, 101, 2833.