Rate constants for the reaction of cumylperoxyl radicals with Bu3SnH and (TMS)3SiH

Chemical Communications

Volumn , Issue 5, 1999, Pages 405-406

  Chatgilialoglu, Chryssostomos ^a   Timokhin, Vitaliy I ^b   Zaborovskiy, Andriy B ^b   Lutsyk, Daria S ^b   Prystansky, Ruslan E ^b  

^a CNR   (Italy)

^b INSTITUTE OF HYDROBIOLOGY   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

CUMENE HYDROPEROXIDE; HYDROCARBON; RADICAL;

ARTICLE; CHEMICAL REACTION KINETICS; OXIDATION;

EID: 0033531448     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808894b     Document Type: Article

References (32)

1. (a) For example, see: D. P. Curran, N. Porter and B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1995; W. B. Motherwell and D. Crich, Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992;
2. (a) For example, see: D. P. Curran, N. Porter and B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1995; W. B. Motherwell and D. Crich, Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1992;
3. 3SiH, see: C. Chatgilialoglu, Acc. Chem. Res., 1992, 25, 188; C. Chatgilialoglu, C. Ferreri and T. Gimisis, in The Chemistry of Organic Silicon Compounds, ed. S. Rappoport and Y. Apeloig, Wiley, London, 1998, vol. 2, pp. 1539-1579.
4. 3SiH, see: C. Chatgilialoglu, Acc. Chem. Res., 1992, 25, 188; C. Chatgilialoglu, C. Ferreri and T. Gimisis, in The Chemistry of Organic Silicon Compounds, ed. S. Rappoport and Y. Apeloig, Wiley, London, 1998, vol. 2, pp. 1539-1579.
5. A terminology introduced by Barton. For example, see: D. H. R. Barton, Aldrichim. Acta, 1990, 23, 3; D. H. R. Barton and S. I. Parekh, Half a Century of Free Radical Chemistry, CUP, Cambridge, UK, 1993.
6. A terminology introduced by Barton. For example, see: D. H. R. Barton, Aldrichim. Acta, 1990, 23, 3; D. H. R. Barton and S. I. Parekh, Half a Century of Free Radical Chemistry, CUP, Cambridge, UK, 1993.
7. For some representative reviews, see: K. U. Ingold, Acc. Chem. Res., 1969, 2, 1; N. A. Porter, in Organic Peroxides, ed. W. Ando, Wiley, Chichester, 1992; C. von Sonntag and H.-P. Schuchmann, Angew. Chem., Int. Ed. Engl., 1991, 30, 1229; C. Walling, in Active Oxygen in Chemistry, ed. C. S. Foote, J. C. Valentine, A. Greenberg and J. F. Liebman, Blackie, London, 1995, pp. 24-65.
8. For some representative reviews, see: K. U. Ingold, Acc. Chem. Res., 1969, 2, 1; N. A. Porter, in Organic Peroxides, ed. W. Ando, Wiley, Chichester, 1992; C. von Sonntag and H.-P. Schuchmann, Angew. Chem., Int. Ed. Engl., 1991, 30, 1229; C. Walling, in Active Oxygen in Chemistry, ed. C. S. Foote, J. C. Valentine, A. Greenberg and J. F. Liebman, Blackie, London, 1995, pp. 24-65.
9. For some representative reviews, see: K. U. Ingold, Acc. Chem. Res., 1969, 2, 1; N. A. Porter, in Organic Peroxides, ed. W. Ando, Wiley, Chichester, 1992; C. von Sonntag and H.-P. Schuchmann, Angew. Chem., Int. Ed. Engl., 1991, 30, 1229; C. Walling, in Active Oxygen in Chemistry, ed. C. S. Foote, J. C. Valentine, A. Greenberg and J. F. Liebman, Blackie, London, 1995, pp. 24-65.
10. For some representative reviews, see: K. U. Ingold, Acc. Chem. Res., 1969, 2, 1; N. A. Porter, in Organic Peroxides, ed. W. Ando, Wiley, Chichester, 1992; C. von Sonntag and H.-P. Schuchmann, Angew. Chem., Int. Ed. Engl., 1991, 30, 1229; C. Walling, in Active Oxygen in Chemistry, ed. C. S. Foote, J. C. Valentine, A. Greenberg and J. F. Liebman, Blackie, London, 1995, pp. 24-65.
11. For example, see: G. L. Hill and G. M. Whitesides, J. Am. Chem. Soc., 1974, 96, 870; D. H. R. Barton, D. Crich and W. B. Motherwell, J. Chem. Soc., Chem. Commun., 1985, 1066; H. C. Brown, M. M. Midland and G. W. Kabalka, Tetrahedron, 1986, 42, 5523.
12. For example, see: G. L. Hill and G. M. Whitesides, J. Am. Chem. Soc., 1974, 96, 870; D. H. R. Barton, D. Crich and W. B. Motherwell, J. Chem. Soc., Chem. Commun., 1985, 1066; H. C. Brown, M. M. Midland and G. W. Kabalka, Tetrahedron, 1986, 42, 5523.
13. For example, see: G. L. Hill and G. M. Whitesides, J. Am. Chem. Soc., 1974, 96, 870; D. H. R. Barton, D. Crich and W. B. Motherwell, J. Chem. Soc., Chem. Commun., 1985, 1066; H. C. Brown, M. M. Midland and G. W. Kabalka, Tetrahedron, 1986, 42, 5523.
14. E. Nakamura, T. Inubushi, S. Aoki and D. Machii, J. Am. Chem. Soc., 1991, 113, 8980; S. Moutel and J. Prandi, Tetrahedron Lett., 1994, 35, 8163; S. Mayer and J. Prandi, Tetrahedron Lett., 1996, 37, 3117; M. Sawamura, Y. Kawaguchi, K. Sato and E. Nakamura, Chem. Lett., 1997, 705; M. Sawamura, Y. Kawaguchi and E. Nakamura, Synlett, 1997, 801.
15. E. Nakamura, T. Inubushi, S. Aoki and D. Machii, J. Am. Chem. Soc., 1991, 113, 8980; S. Moutel and J. Prandi, Tetrahedron Lett., 1994, 35, 8163; S. Mayer and J. Prandi, Tetrahedron Lett., 1996, 37, 3117; M. Sawamura, Y. Kawaguchi, K. Sato and E. Nakamura, Chem. Lett., 1997, 705; M. Sawamura, Y. Kawaguchi and E. Nakamura, Synlett, 1997, 801.
16. E. Nakamura, T. Inubushi, S. Aoki and D. Machii, J. Am. Chem. Soc., 1991, 113, 8980; S. Moutel and J. Prandi, Tetrahedron Lett., 1994, 35, 8163; S. Mayer and J. Prandi, Tetrahedron Lett., 1996, 37, 3117; M. Sawamura, Y. Kawaguchi, K. Sato and E. Nakamura, Chem. Lett., 1997, 705; M. Sawamura, Y. Kawaguchi and E. Nakamura, Synlett, 1997, 801.
17. E. Nakamura, T. Inubushi, S. Aoki and D. Machii, J. Am. Chem. Soc., 1991, 113, 8980; S. Moutel and J. Prandi, Tetrahedron Lett., 1994, 35, 8163; S. Mayer and J. Prandi, Tetrahedron Lett., 1996, 37, 3117; M. Sawamura, Y. Kawaguchi, K. Sato and E. Nakamura, Chem. Lett., 1997, 705; M. Sawamura, Y. Kawaguchi and E. Nakamura, Synlett, 1997, 801.
18. E. Nakamura, T. Inubushi, S. Aoki and D. Machii, J. Am. Chem. Soc., 1991, 113, 8980; S. Moutel and J. Prandi, Tetrahedron Lett., 1994, 35, 8163; S. Mayer and J. Prandi, Tetrahedron Lett., 1996, 37, 3117; M. Sawamura, Y. Kawaguchi, K. Sato and E. Nakamura, Chem. Lett., 1997, 705; M. Sawamura, Y. Kawaguchi and E. Nakamura, Synlett, 1997, 801.
19. For example, see: D. L. Boger and J. A. McKie, J. Org. Chem., 1995, 60, 1271.
20. E. Nakamura, K. Sato and Y. Imanishi, Synlett, 1995, 525.
21. K. A. Tallman, C. Tronche, D. J. Yoo and M. M. Greenberg, J. Am. Chem. Soc., 1998, 120, 4903.
22. E. T. Denisov and I. V. Khudyakov, Chem. Rev., 1987, 87, 1313; E. T. Denisov, Liquid-Phase Reaction Rate Constants, Plenum, New York, 1974; N. M. Emanuel, E. T. Denisov and Z. K. Maizus, Liquid Phase Oxidation of Hydrocarbons, Plenum, New York, 1967.
23. E. T. Denisov and I. V. Khudyakov, Chem. Rev., 1987, 87, 1313; E. T. Denisov, Liquid-Phase Reaction Rate Constants, Plenum, New York, 1974; N. M. Emanuel, E. T. Denisov and Z. K. Maizus, Liquid Phase Oxidation of Hydrocarbons, Plenum, New York, 1967.
24. N. M. Emanuel, E. T. Denisov and Z. K. Maizus, Liquid Phase Oxidation of Hydrocarbons, Plenum, New York, 1967.
25. J. A. Howard, Y. Ohkatsu, J. H. B. Chenier and K. U. Ingold, Can. J. Chem., 1973, 51, 1543; J. H. B. Chenier, S. B. Tong and J. A. Howard, Can. J. Chem., 1978, 56, 3047; S. Korcek, J. H. B. Chenier, J. A. Howard and K. U. Ingold, Can. J. Chem., 1972, 50, 2285.
26. J. A. Howard, Y. Ohkatsu, J. H. B. Chenier and K. U. Ingold, Can. J. Chem., 1973, 51, 1543; J. H. B. Chenier, S. B. Tong and J. A. Howard, Can. J. Chem., 1978, 56, 3047; S. Korcek, J. H. B. Chenier, J. A. Howard and K. U. Ingold, Can. J. Chem., 1972, 50, 2285.
27. J. A. Howard, Y. Ohkatsu, J. H. B. Chenier and K. U. Ingold, Can. J. Chem., 1973, 51, 1543; J. H. B. Chenier, S. B. Tong and J. A. Howard, Can. J. Chem., 1978, 56, 3047; S. Korcek, J. H. B. Chenier, J. A. Howard and K. U. Ingold, Can. J. Chem., 1972, 50, 2285.
28. J. P. Van Hook and A. V. Tobolsky, J. Am. Chem. Soc., 1958, 80, 779; E. Niki, Y. Kamija and N. Ohta, Bull. Chem. Soc. Jpn., 1969, 42, 3220.
29. J. P. Van Hook and A. V. Tobolsky, J. Am. Chem. Soc., 1958, 80, 779; E. Niki, Y. Kamija and N. Ohta, Bull. Chem. Soc. Jpn., 1969, 42, 3220.
30. D. G. Hendry, J. Am. Chem. Soc., 1967, 89, 5433.
31. C. E. Boozer, G. S. Hammond, C. E. Hamilton and J. N. Sen, J. Am. Chem. Soc., 1955, 77, 3233.
32. C. Chatgilíaloglu, Chem. Rev., 1995, 95, 1229.