Radical clock reactions under Pseudo-first-order conditions using catalytic quantities of dipnenyl diselenide. A 77Se- and 119Sn-NMR study of the reaction of tributylstannane and diphenyl diselenide

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2368-2373

  Crich, David ^a   Jiao, Xian Yun ^a   Yao, Qingwei ^a   Harwood, John S ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000580536     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo950857s     Document Type: Article

References (69)

1. (a) Motherwell, W B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992.
2. (b) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986.
3. (c) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1992; Vol. 4, pp 715, 779.
4. (d) Curran, D. P. Synthesis 1988, 417, 489.
5. (e) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
6. (f) Ramaiah, M. Tetrahedron 1987, 43, 3541 and references therein.
7. (a) Lanholt-Bornstein New Series, Vol. 13abc, Fischer, H., Ed., Springer Verlag: Berlin, 1983, 1984, 1985.
8. (b) Ingold, K. U.; Griller, D. Acc. Chem. Res. 1980, 13, 317.
9. (c) Newcomb. M. Tetrahedron 1993, 49, 1151.
10. Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739.
11. (a) Newcomb, M.; Varick, T. R.; Ha, C.; Manek, M. B.; Yue, X. J. Am. Chem. Soc. 1992, 114, 8108.
12. (b) Martin-Esker, A. A.; Johnson, C. C.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 1994, 116, 9174.
13. Crich, D.; Yao, Q. J. Org. Chem. 1995, 60, 84.
14. (a) Allen, R. P.; Roberts, B. P.; Willis, C.; R. J. Chem. Soc., Chem. Commun. 1989, 1387
15. (b) Cole, S. J.; Kirwan, J. N.; Roberts, B. P.; Willis, C. R. J. Chem. Soc., Perkin Trans. 1 1991, 103.
16. (c) Dang, H.-S.; Roberts, B. P. Tetrahedron Lett. 1995, 36, 2875.
17. For early examples of this principle involving decarbonylation of aldehydes catalyzed by thiols see: (a) Harris, E. F. P.; Waters, W. A. Nature 1952, 170, 212. (b) Harris, E. F. P.; Waters, W. A. Discussions Farad. Soc. 1953, 24, 221. (c) Berman, J. D.; Stanley, J. H.; Sherman, W. V.; Cohen, S. G. J. Am. Chem. Soc. 1963, 85, 4010.
18. For early examples of this principle involving decarbonylation of aldehydes catalyzed by thiols see: (a) Harris, E. F. P.; Waters, W. A. Nature 1952, 170, 212. (b) Harris, E. F. P.; Waters, W. A. Discussions Farad. Soc. 1953, 24, 221. (c) Berman, J. D.; Stanley, J. H.; Sherman, W. V.; Cohen, S. G. J. Am. Chem. Soc. 1963, 85, 4010.
19. For early examples of this principle involving decarbonylation of aldehydes catalyzed by thiols see: (a) Harris, E. F. P.; Waters, W. A. Nature 1952, 170, 212. (b) Harris, E. F. P.; Waters, W. A. Discussions Farad. Soc. 1953, 24, 221. (c) Berman, J. D.; Stanley, J. H.; Sherman, W. V.; Cohen, S. G. J. Am. Chem. Soc. 1963, 85, 4010.
20. An alternative explanation for this type of catalysis has recently been advanced: Zavitsas, A. A.; Chatgilialoglu, C. J. Am. Chem. Soc. 1995, 117, 10645.
21. Paulmier, C. Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986; p 26.
22. Newcomb, M.; Manek, M. B.; Glenn, A. G. J. Am. Chem. Soc. 1991, 113, 949.
23. (a) Crich, D.; Fortt, S. M. Tetrahedron Lett. 1988, 29, 2580.
24. (b) Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581.
25. (c) Crich, D.; Eustace, K. A.; Ritchie, T. J. Heterocycles 1989, 28, 67.
26. (d) Crich, D.; Eustace, K. A.; Fortt, S. M.; Ritchie, T. J. Tetrahedron 1990, 46, 2135.
27. (e) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun. 1989, 1366.
28. (f) Batty, D.; Crich, D. Synthesis 1990, 273.
29. (g) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875.
30. (h) Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875.
31. (i) Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193.
32. (j) Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3205.
33. (k) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377.
34. (l) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1989, 54, 1777.
35. (m) Boger, D. L.; Mathvink, R. J. J. Am. Chem. Soc 1990, 112, 4003.
36. (n) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442.
37. (o) Boger, D. L.; Mathvink, R. J. J. Am. Chem. Soc. 1990, 112, 4008.
38. (p) Curran, D. P.; Liu, H. J. Org. Chem. 1991, 56, 3463.
39. McFarlane, H. C. E.; McFarlane, W In NMR of Newly Accessible Nuclei; Laszlo, P., Ed.; Academic: New York, 1983, Vol. 2, p 275.
40. (a) Harris, R. K.; Kennedy, J. D.; McFarlane, W. In NMR and the Periodic Table; Harris, R. K., Mann, B. E., Eds.; Academic: London, 1978; p 342.
41. (b) Smith, P. J.; Tupciauskas, A. P. Annu. Rep. NMR Spectrosc. 1978, 8, 291.
42. 3SnH with slow evolution of a colorless gas and formation of a grey precipitate, presumed to be Se metal.
43. (a) Fukuzawa, S.; Niimoto, Y.; Fujmami, T.; Sakai, S. Heteroat. Chem. 1990, 1, 491.
44. (b) Macmullin, E. C.; Peach, M. E. J. Organomet. Chem. 1973, 52, 355.
45. Ha, C.; Horner, J. M.; Newcomb, M.; Varick, T. R.; Arnold, B. R.; Lusztyk, J. J. Org. Chem. 1993, 58, 1194.
46. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901.
47. Newcomb, M.; Horner, J. H.; Filipowski, M. A.; Ha, C.; Park, S.-U. J. Am. Chem. Soc. 1995, 117, 3674.
48. Errors are given at the 95% confidence interval (3.2σ for the results obtained here with a small data set and 2σ for those of Newcomb with a much larger data set).
49. 4
50. Griller, D.; Kanabus-Kaminska, J. M.; Maccoll, A. J. Mol. Struct. (THEOCHEM) 1988, 163, 125.
51. See footnote 34 in ref 10.
52. -1 rather than that of 78 used in ref 10.
53. Carlsson, D. J.; Ingold, K. U. J. Am. Chem. Soc. 1968, 94, 6059.
54. As noted by Newcomb the activation parameters in eqs 8 and 9 are such that trapping by PhSeH must be partially diffusion controlled in low viscosity solvents. For a full discussion of this point see ref 4a.
55. Korth, H.-G.; Sustmann, R.; Groninger, K. S.; Leisung, M.; Giese, B. J. Org. Chem. 1988, 53, 4364.
56. (a) Adlington, R. M.; Baldwin, J. E.; Basak, A.; Kozyrod, R. P. J. Chem. Soc., Chem. Commun. 1983, 944.
57. (b) Bonner, W. A.; Robinson, A. J. Am. Chem. Soc. 1950, 72, 354.
58. Smith, E. D.; Mathews, D. M. J. Chem. Ed. 1967, 44, 757.
59. Errors given for the 95% confidence interval (2.3σ).
60. Johnson, C. C.; Horner, J. H.; Tronche, C.; Newcomb, M. J. Am. Chem. Soc 1995, 117, 1684.
61. (a) Beckwith, A. L. J.; Brumby, S. J. Chem. Soc., Perkin Trans. 2 1987, 1801.
62. (b) Dobbs, A. J.; Gilbert, B. C.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1972, 786.
63. (c) Gilbert, B. C.; Trenwith, M.; Dobbs, A. J. J. Chem. Soc., Perkin Trans. 2 1974, 1772.
64. (a) Dupuis, J.; Giese, B.; Ruegge, D.; Fischer, H.; Korth, H.-G.; Sustmann, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 896.
65. (b) Korth, H. G.; Sustmann, R.; Dupuis, J.; Giese. B. J. Chem. Soc., Perkin Trans. 2 1986, 1453.
66. Beckwith, A. L. J.; Gara, W. G. J. Chem. Soc., Perkin. Trans. 2 1975, 795.
67. Johnson, L. J.; Lusztyk, J.; Wayner, D. D. M.; Abeywickrema, A. N.; Beckwith, A. L. J.; Scaiano, J, C.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 4594.
68. Meyers, A. I.; Collington, E. W. Tetrahedron 1971, 27, 5979.
69. Beckwith, A. L J.; Duggan, P. J. J. Chem. Soc., Perkin Trans. 1 1993, 1672.