Influence of the size of the formed cycle on the reactivity of free radicals in cyclization reactions

Russian Chemical Bulletin

Volumn 51, Issue 6, 2002, Pages 949-960

  Denisova, T G ^a   Denisov, E T ^a  

^a INSTITUTE OF PROBLEMS OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

Activation energy; Activation entropy; Cyclization; Enthalpy of reaction; Free radical; Parabolic model; Reaction rate constant; Reactivity

Indexed keywords

ALKENE; FREE RADICAL; HYDROCARBON; PARAFFIN;

ARTICLE; ATOM; CYCLIZATION; ENERGY; ENTROPY; MOLECULAR DYNAMICS; MOLECULAR WEIGHT;

EID: 0036341074     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1019697131654     Document Type: Article

References (56)

1. J. W. Wilt, Free Radicals, Ed. J. K. Kochi, Wiley, New York, 1973, 1, 333 pp.
2. D. P. Curran, N. A. Porter, and B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1995.
3. A. L. J. Beckwith and C. H. Schiesser, Tetrahedron, 1985, 41, 3925.
4. D. C. Spellmeyer and K. N. Houk, J. Org. Chem., 1987, 52, 959.
5. C. Chatgilialoglu and P. Renaud, in General Aspects of the Chemistry of Radicals, Ed. Z. B. Alfassi, Wiley, New York, 1999, 501.
6. E. T. Denisov, Kinet. Katal., 1992, 33, 66 [Kinet. Catal., 1992, 33, 50 (Engl. Transl.)].
7. E. T. Denisov, Kinet. Katal., 1992, 33, 66 [Kinet. Catal., 1992, 33, 50 (Engl. Transl.)].
8. E. T. Denisov, Kinet. Katal., 1999, 40, 835 [Kinet. Catal., 1999, 40, 756 (Engl. Transl.)].
9. E. T. Denisov, Kinet. Katal., 1999, 40, 835 [Kinet. Catal., 1999, 40, 756 (Engl. Transl.)].
10. E. T. Denisov and T. G. Denisova, Khim. Fiz., 1998, 17, 83 [Chem. Phys. Reports, 1998, 17, 2105 (Engl. Transl.)].
11. E. T. Denisov and T. G. Denisova, Khim. Fiz., 1998, 17, 83 [Chem. Phys. Reports, 1998, 17, 2105 (Engl. Transl.)].
12. T. G. Denisova and E. T. Denisov, Neftekhimiya, 1998, 38, 15 [Petroleum Chem., 1998, 38, 12 (Engl. Transl.)].
13. T. G. Denisova and E. T. Denisov, Neftekhimiya, 1998, 38, 15 [Petroleum Chem., 1998, 38, 12 (Engl. Transl.)].
14. E. T. Denisov, Usp. Khim., 2000, 69, 166 [Russ. Chem. Rev., 2000, 69, 153 (Engl. Transl.)].
15. E. T. Denisov, Usp. Khim., 2000, 69, 166 [Russ. Chem. Rev., 2000, 69, 153 (Engl. Transl.)].
16. A. L. J. Beckwith and V. W. Bowry, J. Org. Chem., 1989, 54, 2681.
17. A. Effio, D. Griller, K. U. Ingold, A. L. J. Beckwith, and A. K. Serelis, J. Am. Chem. Soc., 1980, 102, 1734.
18. E. C. Friedrich and R. L. Holmstead, J. Org. Chem., 1972, 37, 2550.
19. P. Schmid and K. U. Ingold, J. Am. Chem. Soc., 1978, 100, 2493.
20. A. L. J. Beckwith, I. A. Blair, and G. Phillipou, Tetrahedron Lett., 1974, 26, 2251.
21. D. Lal, G. Griller, S. Husband, and K. U. Ingold, J. Am. Chem. Soc., 1974, 96, 6355.
22. J. W. Wilt, J. Lusztyk, M. Peeran, and K. U. Ingold, J. Am. Chem. Soc., 1988, 110, 281.
23. A. L. J. Beckwith, Tetrahedron, 1981, 37, 3073.
24. A. L. J. Beckwith, T. Lawrence, and A. K. Serelis, J. Chem. Soc., Chem. Commun., 1980, 11, 484.
25. A. L. J. Beckwith, C. J. Easton, T. Lawrence, and A. K. Serelis, Aust. J. Chem., 1983, 36, 545.
26. A. L. J. Beckwith and C. H. Schiesser, Tetrahedron, 1985, 41, 3925.
27. C. Walling and A. Cioffari, J. Am. Chem. Soc., 1972, 94, 6064.
28. A. L. J. Beckwith and T. Lawrence, J. Chem. Soc., Perkin Trans. 2, 1979, 11, 1535.
29. A. L. J. Beckwith and V. W. Bowry, J. Org. Chem., 1988, 53, 1632.
30. J. W. Wilt, Tetrahedron, 1985, 41, 3979.
31. A. L. J. Beckwith and G. Moad, J. Chem. Soc., Perkin Trans. 2, 1975, 15, 1726.
32. M. Newcomb, T. R. Varick, C. Ha, M. B. Manek, and X. Yue, J. Am. Chem. Soc., 1992, 114, 8158.
33. C. Ha, J. H. Horner, M. Newcomb, T. R. Varick, B. R. Arnold, and J. Lusztyk, J. Org. Chem., 1993, 58, 1194.
34. C. C. Johnson, J. H. Horner, C. Tronche, and M. Newcomb, J. Am. Chem. Soc., 1995, 117, 1684.
35. M. Newcomb, J. H. Horner, M. A. Filipkowski, C. Ha, and Seung-Un Park, J. Am. Chem. Soc., 1995, 117, 3674.
36. P. E. Pigou, J. Org. Chem., 1989, 54, 4943.
37. J. W. Wilt, S. N. Massie, and R. B. Dabek, J. Org. Chem., 1970, 35, 2803.
38. F. MacCorquodale and J. C. Walton, J. Chem. Soc., Perkin Trans. 1, 1989, 2, 347.
39. A. L. J. Beckwith and S. A. Glover, Aust. J. Chem., 1987, 40, 157.
40. T. W. Smith and G. B. Butter, J. Org. Chem., 1978, 43, 6.
41. A. L. J. Beckwith, I. A. Blair, and G. Phillipou, J. Am. Chem. Soc., 1974, 96, 1613.
42. A. C. Hindson, F. MacCorquodale, and J. C. Walton, J. Chem. Soc., Perkin Trans. 2, 1993, 5, 871.
43. C. F. Sturino and A. G. Fallis, J. Org. Chem., 1994, 59, 6514.
44. W. R. Dolbier, Chem. Rev., 1996, 96, 1557.
45. J. W. Wilt, J. Am. Chem. Soc., 1981, 103, 5251.
46. A. L. J. Beckwith and G. Moad, J. Chem. Soc., Chem. Commun., 1974, 12, 472.
47. J. Lusztyk, B. Maillard, S. Deycard, D. A. Lindsay, and K. U. Ingold, J. Org. Chem., 1987, 52, 3509.
48. C. Chatgilialoglu, C. Ferreri, and A. Sommazzi, J. Am. Chem. Soc., 1996, 118, 7223.
49. A. L. J. Beckwith, V. W. Bowry, and C. H. Schiesser, Tetrahedron, 1991, 47, 121.
50. S. G. Lias, J. F. Liebman, R. D. Levin, S. A. Kafafi, and E. S. Stein, NIST Positive Ion Energetics - Ver. 2.0. NIST Standard Reference Database 19A, Gaithersburg, 1993.
51. S. W. Benson, Thermochemical Kinetics, Wiley, New York, 1968.
52. E. S. Domalski and E. D. Hearing, J. Phys. Chem. Ref. Data, 1993, 22, 805.
53. V. E. Tumanov and E. T. Denisov, Neftekhimiya, 2001, 41, 109 [Petroleum Chem., 2001, 41 (Engl. Transl.)].
54. V. E. Tumanov and E. T. Denisov, Neftekhimiya, 2001, 41, 109 [Petroleum Chem., 2001, 41 (Engl. Transl.)].
55. T. G. Denisova and E. T. Denisov, Kinet. Katal., 2001, 42, 684 [Kinet. Catal., 2001, 42, No. 5 (Engl. Transl.)].
56. T. G. Denisova and E. T. Denisov, Kinet. Katal., 2001, 42, 684 [Kinet. Catal., 2001, 42, No. 5 (Engl. Transl.)].