A kinetic evaluation of carbon-hydrogen, carbon-carbon, and carbon-silicon bond activation in benzylic radical cations

Journal of the American Chemical Society

Volumn 120, Issue 2, 1998, Pages 284-297

  Freccero, Mauro ^a   Pratt, Albert ^a   Albini, Angelo ^b   Long, Conor ^a  

^a DUBLIN CITY UNIVERSITY   (Ireland)

^b UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL DERIVATIVE; CARBON; CATION; HYDROGEN; RADICAL; SILICON;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; EVALUATION AND FOLLOW UP; KINETICS; NONHUMAN; OXIDATION REDUCTION REACTION;

EID: 0032554060     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970940s     Document Type: Article

References (44)

1. (a) Electron-Transfer Reactions in Organic Chemistry; Eberson L., Ed.; Springer: Berlin, Heidelberg, New York, 1987; see also references therein cited,
2. (b) Advances in Electron-Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: Greenwich, CT, 1991-94; Vols. 1-4.
3. (c) Top. Curr. Chem. Mattay, J., Ed.; 1990-94, 750, 158, 159, 163, 168, 169.
4. (d) Photoinduced Electron Transfer, Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Parts A, B, and C and references therein,
5. (e) Photochemical Key Steps in Organic Synthesis; Mattay, J., Griesbeck, A.; Eds.; VCH: Weinheim, 1994.
6. (f) Chiu, F.-T.; Ullrich, J. W.; Mariano, P. S. J. Org. Chem. 1984, 49, 228.
7. (g) Albini, A.; Mella, M.; Freccero, M.; Tetrahedron 1994, 50, 575.
8. (h) Mella, M.; d'Alessandro, N.; Freccero, M.; Albini, A. J. Chem. Soc., Perkin Trans. 2 1993, 515.
9. (i) Fagnoni, M.; Mella, M.; Albini, A. J. Am. Chem. Soc. 1995, 117, 7877.
10. (j) Albini, A.; Mella, M. Tetrahedron 1986, 42, 6219.
11. (k) Albini, A.; Fasani, E.; Mella, M. J. Am. Chem. Soc. 1986, 108, 4119.
12. (1) Mariano, P. S.; Stavinoha, J. L. In Synthetic Organic Photochemistry: Horspool, W. M., Ed.; Plenum Press: London, 1984.
13. (m) Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233.
14. (n) Gaillard, R. E.; Whitten, D. G. Acc. Chem. Res. 1996, 29, 292.
15. (o) Albini, A.; Siviero, E.; Mella, M.; Long, C.; Pratt, A.; J. Chem. Soc., Perkin Trans. 2 1995, 1895.
16. Lewis, F. D. Acc. Chem. Res. 1986, 19, 401.
17. Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 7472.
18. Ohga, K;.Yoon, U. C.; Mariano, P. S. J. Org. Chem. 1984, 49, 213.
19. Dinnocenzo, J. P.; Fand, S.; Goodman, J. L.; Gould, I. R.; Todd, W. R.; Mattes, S. L. J. Am. Chem. Soc. 1989, 111, 8973.
20. (a) d'Alessandro, N.; Albini, A.; Mariano, P. S. J. Org. Chem. 1993, 58, 937.
21. (b) Budac, D.; Wan, P. J. Photochem. Photobiol., A: Chem. 1992, 67, 135.
22. (c) Meiggs, T. O.; Grossweiner, L. L; Miller, S. I. J. Am. Chem. Soc. 1972, 94, 7981.
23. (d) Steenken, S.; Warren, C. J.; Gilbert, B. C. J. Chem. Soc., Perkin Trans. 2 1990, 335.
24. (e) Davidson, R. S.; Steiner, P. R. J. Chem. Soc., Perkin Trans. 2 1972, 1557.
25. Dinnocenzo, J. P.; Banach, I. E. J. Am. Chem. Soc. 1989, 111, 8646.
26. Baciocchi, E.; Del Giacco, T.; Elisei, F. J. Am. Chem. Soc, 1993, 115, 12290.
27. Zhana, X.; Yeh, S.-R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, D.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 4211.
28. Baciocchi, E.; Mattioli, M.; Romano, R.; Ruzziconi, R. J. Org. Chem. 1991, 56, 7154.
29. Tolbert, L. M.; Khanna, R. K.; Popp, A. E.; Gelbaum, L.; Bottomley, L. A. J. Am. Chem. Soc. 1990, 112, 2373.
30. (a) Dockery, K. P.; Dinnocenzo, J. P.; Farid, S.; Goodmann, J. L.; Gould, I. R.; Todd, W. P. J. Am. Chem. Soc. 1997, 779, 1876.
31. (b) Todd, W. R.; Dinnocenzo, J. P.; Fand, S.; Goodman, J. L.; Gould, I. R. J. Am. Chem. Soc. 1991, 113, 3601.
32. (c) Dinnocenzo, J. P.; Fand, S.; Goodman, J. L.; Gould, I. R.; Todd, W. P. Mol. Cryst. Liq. Cryst. 1991, 194, 151.
33. Arnold, D. R.; Maroulis, A. J. J. Am. Chem. Soc. 1976, 98, 5931.
34. (a) Okamoto, A.; Arnold, D. R. Can. J. Chem. 1985, 63, 2340.
35. (b) Okamoto, A.; Snow, M. S.; Arnold, D. R. Tetrahedron 1986, 42, 6175.
36. Popielarz, R.; Arnold, D. R. J. Am. Chem. Soc. 1990, 112, 3068.
37. (a) Maslak, P.; Chapman, W. H., Jr.; Vallombroso, T. M., Jr.; Watson, B. A. J. Am. Chem. Soc. 1995, 117, 12380.
38. (b) Maslak, P. Top. Curr. Chem. 1993, 168, 143.
39. (c) Maslak, P.; Asel, S. L. J. Am. Chem. Soc. 1988, 110, 8260.
40. (d) Maslak, P.; Vallombroso, T. M.; Chapman, W. H., Jr.; Narvaez, J. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 73.
41. (a) Anne, A.; Hapiout, P.; Moiroux, J.; Neta, P.; Savéant, J. M. J. Am. Chem. Soc. 1992, 114, 4694.
42. (b) Anne, A.; Fraoua, S.; Moiroux, J.; Savéant, J. M. J. Am. Chem. Soc. 1996, 118, 3938.
43. ̇+, we have not considered it worthwhile to attempt a similar analysis.
44. Parker, V. D.; Tilset, M. J. Am. Chem. Soc. 1991, 113, 8778.