The study of the kinetics of intramolecular radical cyclizations of acylsilanes via the intramolecular competition method

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 618-628

  Jiaang, Weir Torn ^a   Lin, Hsien Chang ^a   Tang, Kuo Hsiang ^a   Chang, Lih Bin ^a   Tsai, Yeun Min ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; REACTION ANALYSIS;

EID: 0033593375     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982079k     Document Type: Article

References (74)

1. (a) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: New York, 1995.
2. (b) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856.
3. (a) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 1, pp 161-310.
4. (b) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 779-831.
5. (c) Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
6. Flies, M. F.; Lalande, R.; Maillard, B. Tetrahedron Lett. 1976, 439-442.
7. (a) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 108, 2116-2117.
8. (b) Tsang, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1986, 708, 8102-8104.
9. (c) Tsang, R.; Dickson, J. K., Jr.; Pak, H.; Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1987, 109, 3484-3486.
10. (d) Fraser-Reid, B.; Vite, G. D.; Yeung, B.-W. A.; Tsang, R. Tetrahedron Lett. 1988, 29, 1645-1648.
11. (e) Dickson, J. K., Jr.; Tsang, R.; Llera, J. M.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 5350-5356.
12. (f) Walton, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 113, 5791-5799.
13. (a) Paquette, L. A.; Ra, C. S.; Silvestri, T. W. Tetrahedron 1989, 45, 3099-3106.
14. (b) Knapp, S.; Gibson, F. S.; Choe, Y. H. Tetrahedron Lett. 1990, 38, 5397-5400.
15. (c) Knapp, S.; Gibson, F. S. J. Org. Chem. 1992, 57, 4802-4809.
16. (d) Grissom, J. W.; Klingberg, D. J. Org. Chem. 1993, 58, 6559-6564.
17. (e) Grissom, J. W.; Klingberg, D.; Meyenburg, S.; Stallman, B. L. J. Org. Chem. 1994, 59, 7876-7888.
18. (f) Clive, D. L. J.; Postema, M. H. D. J. Chem. Soc., Chem. Commun. 1993, 429-430.
19. (g) Jung, M. E.; Choe, S. W. T. Tetrahedron Lett. 1993, 34, 6247-6250.
20. (h) Hays, D. S.; Fu, G. C. J. Am. Chem. Soc. 1995, 117, 7283-7284.
21. (i) Davin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1998, 39, 833-836.
22. (a) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 111, 230-234.
23. (b) Beckwith, A. L. J.; Hay, B. P. J. Am. Chem. Soc. 1989, 111, 2674-2681.
24. (c) Beckwith, A. L. J.; Raner, K. D. J. Org. Chem. 1992, 57, 4954-4962.
25. Beckwith, A. L. J. Tetrahedron 1981, 37, 3073-3100.
26. Lusztyk, J.; Maillard, B.; Deycard, S.; Lindsay, D. A.; Ingold, K. U. J. Org. Chem. 1987, 52, 3509-3514.
27. (a) Curran, D. P.; Liu, H. J. Org. Chem. 1991, 56, 3463-3465.
28. (b) Curran, D. P.; Palovich, M. Synlett 1992, 631-632.
29. (c) Curran, D. P.; Diederichsen, U.; Palovich, M. J. Am. Chem. Soc. 1997, 119, 4797-4804.
30. Diederichsen, U.; Curran, D. P. J. Organomet. Chem. 1997, 537, 9-12.
31. (a) Curran, D. P.; Xu, J.; Lazzarini, E. J. Am. Chem. Soc. 1995, 117, 6603-6604.
32. (b) Curran, D. P.; Xu, J. Y.; Lazzarini, E. J. Chem. Soc., Perkin Trans. 1 1995, 3049-3059.
33. Beckwith, A. L. J.; Blair, I. A.; Phillipou, G. Tetrahedron Lett. 1974, 2251-2254.
34. Kim, S.; Jon, S. Y. J. Chem. Soc., Chem. Commun. 1996, 1335-1336.
35. (a) Giese, B.; Heinrich, N.; Horler, H.; Koch, W.; Schwarz, H. Chem. Ber. 1986, 119, 3528-3835.
36. (b) Wollowitz, S.; Halpern, J. J. Am. Chem. Soc. 1984, 106, 8319-8321.
37. (c) Wollowitz, S.; Halpern, J. J. Am. Chem. Soc. 1988, 110, 3112-3120.
38. (d) Lindsay, D. A.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1984, 106, 7087-7093.
39. (a) Tsai, Y.-M.; Cherng, C.-D. Tetrahedron Lett. 1991, 32, 3515-3518.
40. (b) Tsai, Y.-M.; Tang, K.-H.; Jiaang, W.-T. Tetrahedron Lett. 1993, 34, 1303-1306.
41. (c) Curran, D. P.; Jiaang, W.-T.; Palovich, M.; Tsai, Y.-M. Synlett 1993, 403-404.
42. (d) Tsai, Y.-M.; Chang, S.-Y. J. Chem. Soc., Chem. Commun. 1995, 981-982.
43. (e) Chuang, T.-H.; Fang, J.-M.; Jiaang, W.-T.; Tsai, Y.-M. J. Org. Chem. 1996, 67, 1794-1805.
44. (f) Tsai, Y.-M.; Tang, K.-H.; Jiaang, W.-T. Tetrahedron Lett. 1996, 37, 7767-7770.
45. (g) Tsai, Y.-M.; Nieh, H.-C.; Pan, J.-S.; Hsiao, D.-D. J. Chem. Soc., Chem. Commun. 1996, 2469-2470.
46. (h) Chang, S.-Y.; Jiaang, W.-T.; Cherng, C.-D.; Tang, K.-H.; Huang, C.-H.; Tsai, Y.-M. J. Org. Chem. 1997, 62, 9089-9098.
47. (a) Dalton, J. C.; Bourque, R. A. J. Am. Chem. Soc. 1981, 103, 699-700.
48. (b) Harris, J. M.; MacInnes, I.; Walton, J. C.; Maillard, B. J. Organomet. Chem. 1991, 403, C25-C28.
49. (c) Tsai, Y.-M.; Ke, B.-W. J. Chin. Chem. Soc. (Taipei) 1993, 40, 641-642.
50. (d) Robertson, J.; Burrows, J. N. Tetrahedron Lett. 1994, 35, 3777-3780.
51. Jackson, R. A. J. Organomet. Chem. 1979, 166, 17-19.
52. Beckwith, A. L. J.; Easton, C. J.; Lawrence, T.; Serelis, A. K. Aust. J. Chem. 1983, 36, 545-556.
53. Lusztyk, J.; Maillard, B.; Deycard, S.; Lindsay, D. A.; Ingold, K. U. J. Og. Chem. 1987, 52, 3509-3514.
54. Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Chem. Commun. 1974, 472-473.
55. Davey, A. E.; Parsons, A. F.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1989, 1853-1858.
56. McMurry, J. Org. React. 1976, 24, 187-224.
57. Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 287-290.
58. (a) Ho, T.-L.; Ho, H. C.; Wong, C. M. J. Chem. Soc., Chem. Commun. 1972, 791.
59. (b) Ho, H. C.; Ho, T.-L.; Wong, C. M. Can. J. Chem. 1972, 50, 2718-2721.
60. (a) Beckwith, A. L. J.; Lawrence, T. J. Chem. Soc., Perkin Trans. 2 1979, 1535-1539.
61. (b) Capon, B.; McManus, S. P. Neighboring Group Participation; Plenum Publishing: New York, 1976; Vol. 1, pp 58-75.
62. (c) Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183-278.
63. Battioni, J.-P.; Chodkiewicz, W. Bull. Soc. Chim. Fr. 1971, 1824-1833.
64. For stereoselectivity of cycloalkyl radicals in general, see the following: Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: New York, 1996; Chapter 3, p 116.
65. Beckwith, A. L. J.; Zimmermann, J. J. Org. Chem. 1991, 56, 5791-5796.
66. Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy, 3rd ed.; VCH: Weinhein, 1990; p 115.
67. Beckwith, A. L. J.; Lawrence, T.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 484-485.
68. Ingold, K. U.; Lusztyk, J.; Scaiano, J. C. J. Am. Chem. Soc. 1984, 106, 343-348.
69. Carlsson, D. J.; Ingold, K. U. J. Am. Chem. Soc. 1968, 90, 7047-7055.
70. Beckwith, A. L. J.; Pigou, P. E. Aust. J. Chem. 1986, 39, 77-87.
71. (a) Shono, T.; Nishiguchi, I.; Ohmizu, H.; Mitani, M. J. Org. Chem. 1978, 100, 545-550.
72. (b) Crandall, J. K.; Magaha, H. S. J. Org. Chem. 1982, 47, 5368-5371.
73. Pouchert, C. J. The Aldrich Library of NMR Spectrum; 2nd ed.; Aldrich Chemical: Milwaukee, 1983; 1(1), 51A, 51B.
74. Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140-3154.