The β-sulfur substituent effect in radical reactions. Chlorine-atom abstraction from alkyl 2-chloroethyl sulfides, hydrogen-atom abstraction from dialkyl sulfides and the question of possible 1,4-hydrogen-atom transfer in β-alkylthioethyl radicals

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 12, 1999, Pages 2691-2700

  Roberts, Brian P ^a   Smits, Teika M ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013205583     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906261k     Document Type: Article

References (64)

1. D. H. R. Barton, W. Hartwig and W. B. Motherwell, J. Chem. Soc., Chem. Commun., 1982, 447.
2. C. Sosa and H. B. Schlegel, J. Am. Chem. Soc., 1987, 109, 7007.
3. D. Crich, A. L. J. Beckwith, C. Chen, Q. Yao, I. G. E. Davison, R. W. Longmore, C. Anaya de Parrodi, L. Quintero-Cortes and J. Sandoval-Ramirez, J. Am. Chem. Soc., 1995, 117, 8757.
4. B. P. Roberts and A. J. Steel, J. Chem. Soc., Perkin Trans. 2, 1994, 2411.
5. M. S. Akhlaq, S. Al-Baghdadi and C. von Sonntag, Carbohydr. Res., 1987, 164, 71.
6. R. D. Grant, P. G. Griffiths, G. Moad, E. Rizzardo and D. H. Solomon, Aust. J. Chem., 1983, 36, 2447.
7. W. K. Busfield, I. D. Grice, I. D. Jenkins and M. J. Monteiro, J. Chem. Soc., Perkin Trans. 2, 1994, 1071.
8. W. K. Busfield, I. D. Grice and I. D. Jenkins, J. Chem. Soc., Perkin Trans. 2, 1994, 1079.
9. B. P. Roberts and A. J. Steel, Tetrahedron Lett., 1993, 34, 5167.
10. P. J. Krusic and J. K. Kochi, J. Am. Chem. Soc., 1971, 93, 846.
11. D. Casarini, L. Grossi, L. Lunazzi and G. Placucci, J. Org. Chem., 1985, 50, 703.
12. L. Lunazzi, G. Placucci and L. Grossi, J. Chem. Soc., Perkin Trans. 2, 1981, 703; L. Lunazzi, G. Placucci and L. Grossi, Tetrahedron, 1983, 39, 159.
13. L. Lunazzi, G. Placucci and L. Grossi, J. Chem. Soc., Perkin Trans. 2, 1981, 703; L. Lunazzi, G. Placucci and L. Grossi, Tetrahedron, 1983, 39, 159.
14. R. M. Marshall, Int. J. Chem. Kinet., 1990, 22, 935.
15. B. Viskolcz, G. Lendvay, T. Körtvélyesi and L. Seres, J. Am. Chem. Soc., 1996, 118, 3006.
16. (a) L. Kaplan, Bridged Free Radicals, Marcel Dekker, New York, 1972, ch. 8;
17. (b) E. Block, Reactions of Organosulfur Compounds, Academic Press, New York, 1978, pp. 189-193.
18. D. L. Tuleen, W. G. Bentrude and J. C. Martin, J. Am. Chem. Soc., 1963, 85, 1938; T. H. Fisher and J. C. Martin, J. Am. Chem. Soc., 1966, 88, 3382; A. Ohno and Y. Ohnishi, Tetrahedron Lett., 1972, 339; J. T. Hepinstall, Jr. and J. A. Kampmeier, J. Am. Chem. Soc., 1973, 95, 1904.
19. D. L. Tuleen, W. G. Bentrude and J. C. Martin, J. Am. Chem. Soc., 1963, 85, 1938; T. H. Fisher and J. C. Martin, J. Am. Chem. Soc., 1966, 88, 3382; A. Ohno and Y. Ohnishi, Tetrahedron Lett., 1972, 339; J. T. Hepinstall, Jr. and J. A. Kampmeier, J. Am. Chem. Soc., 1973, 95, 1904.
20. D. L. Tuleen, W. G. Bentrude and J. C. Martin, J. Am. Chem. Soc., 1963, 85, 1938; T. H. Fisher and J. C. Martin, J. Am. Chem. Soc., 1966, 88, 3382; A. Ohno and Y. Ohnishi, Tetrahedron Lett., 1972, 339; J. T. Hepinstall, Jr. and J. A. Kampmeier, J. Am. Chem. Soc., 1973, 95, 1904.
21. D. L. Tuleen, W. G. Bentrude and J. C. Martin, J. Am. Chem. Soc., 1963, 85, 1938; T. H. Fisher and J. C. Martin, J. Am. Chem. Soc., 1966, 88, 3382; A. Ohno and Y. Ohnishi, Tetrahedron Lett., 1972, 339; J. T. Hepinstall, Jr. and J. A. Kampmeier, J. Am. Chem. Soc., 1973, 95, 1904.
22. (a) J. A. Baban and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1981, 161;
23. (b) V. Diart and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1992, 1761.
24. P. Kaushal, P. L. H. Mok and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1990, 1663.
25. C. Chatgilialoglu, K. U. Ingold and J. C. Scaiano, J. Am. Chem. Soc., 1982, 104, 5123; C. Chatgilialoglu, Acc. Chem. Res., 1992, 25, 188; Chem. Rev., 1995, 95, 1229.
26. C. Chatgilialoglu, K. U. Ingold and J. C. Scaiano, J. Am. Chem. Soc., 1982, 104, 5123; C. Chatgilialoglu, Acc. Chem. Res., 1992, 25, 188; Chem. Rev., 1995, 95, 1229.
27. C. Chatgilialoglu, K. U. Ingold and J. C. Scaiano, J. Am. Chem. Soc., 1982, 104, 5123; C. Chatgilialoglu, Acc. Chem. Res., 1992, 25, 188; Chem. Rev., 1995, 95, 1229.
28. K. S. Chen, I. H. Elson and J. K. Kochi, J. Am. Chem. Soc., 1973, 95, 5341; A. J. Bowles, A. Hudson and R. A. Jackson, Chem. Phys. Lett., 1970, 5, 552.
29. K. S. Chen, I. H. Elson and J. K. Kochi, J. Am. Chem. Soc., 1973, 95, 5341; A. J. Bowles, A. Hudson and R. A. Jackson, Chem. Phys. Lett., 1970, 5, 552.
30. V. Paul and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1988, 1183.
31. A. G. Davies, D. Griller and B. P. Roberts, J. Chem. Soc. B, 1971, 1823; D. Griller and K. U. Ingold, Acc. Chem. Res., 1980, 13, 193; H. Fischer and H. Paul, Acc. Chem. Res., 1987, 20, 200.
32. A. G. Davies, D. Griller and B. P. Roberts, J. Chem. Soc. B, 1971, 1823; D. Griller and K. U. Ingold, Acc. Chem. Res., 1980, 13, 193; H. Fischer and H. Paul, Acc. Chem. Res., 1987, 20, 200.
33. A. G. Davies, D. Griller and B. P. Roberts, J. Chem. Soc. B, 1971, 1823; D. Griller and K. U. Ingold, Acc. Chem. Res., 1980, 13, 193; H. Fischer and H. Paul, Acc. Chem. Res., 1987, 20, 200.
34. P. I. Abell, in Free Radicals, ed. J. K. Kochi, Wiley-Interscience, New York, 1973, vol. 2, ch. 13, pp. 80-84.
35. W. B. Gara and B. P. Roberts, J. Organomet. Chem., 1977, 135, C20.
36. J. Lal, J. Org. Chem., 1961, 26, 971.
37. J. R. Hancock, W. R. Hardstaff, P. A. Johns, R. F. Langler and W. S. Mantle, Can. J. Chem., 1983, 61, 1472.
38. D. Griller, D. C. Nonhebel and J. C. Walton, J. Chem. Soc., Perkin Trans. 2, 1984, 1817.
39. (a) J. Q. Adams, J. Am. Chem. Soc., 1970, 92, 4535;
40. (b) I. Biddles, A. Hudson and J. T. Wiffen, Tetrahedron, 1972, 28, 867;
41. (c) W. B. Gara, B. P. Roberts, B. C. Gilbert, C. M. Kirk and R. O. C. Norman, J. Chem. Res., 1977, 152 (S), 1748 (M).
42. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratman, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Peterson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malik, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzales, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzales, M. Head-Gordon, E. S. Replogle and J. A. Pople, GAUSSIAN 98, Revision A.6, Gaussian Inc., Pittsburgh PA, 1998.
43. L. A. Curtiss, K. Raghavachari and J. A. Pople, J. Chem. Phys., 1993, 98, 1293.
44. (a) Handbook of Chemistry and Physics, 78th edn., ed. D. R. Lide, CRC Press, Boca Raton, 1997-1998;
45. (b) J. Berkowitz, G. B. Ellison and D. Gutman, J. Phys. Chem., 1994, 98, 2744.
46. H. Maskill, The Physical Basis of Organic Chemistry, Oxford University Press, Oxford, 1990, p. 245.
47. D. Griller and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1972, 747; D. Griller and K. U. Ingold, Acc. Chem. Res., 1980, 13, 317; J. C. Walton, J. Chem. Soc., Perkin Trans. 2, 1998, 603.
48. D. Griller and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1972, 747; D. Griller and K. U. Ingold, Acc. Chem. Res., 1980, 13, 317; J. C. Walton, J. Chem. Soc., Perkin Trans. 2, 1998, 603.
49. D. Griller and B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1972, 747; D. Griller and K. U. Ingold, Acc. Chem. Res., 1980, 13, 317; J. C. Walton, J. Chem. Soc., Perkin Trans. 2, 1998, 603.
50. G. Trinquier, J. Am. Chem. Soc., 1992, 114, 6807 and references cited therein.
51. S. G. Lias, J. E. Bartmess, J. F. Liebman, J. L. Holmes, R. D. Levin and W. G. Mallard, J. Phys. Chem. Ref. Data, 1988, 17, Suppl. no. 1.
52. C. Rüchardt, Angew. Chem., Int. Edn. Engl., 1970, 9, 830; B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1996, 2719.
53. C. Rüchardt, Angew. Chem., Int. Edn. Engl., 1970, 9, 830; B. P. Roberts, J. Chem. Soc., Perkin Trans. 2, 1996, 2719.
54. (a) O. Exner, Dipole Moments in Organic Chemistry, Thieme, Stuttgart, 1975;
55. (b) O. Exner, Correlation Analysis of Chemical Data, Plenum Press, New York, 1988.
56. E. Block, Reactions of Organosulfur Compounds, Academic Press, New York, 1978, pp. 141-145.
57. B. C. Gilbert, D. J. Parry and L. Grossi, J. Chem. Soc., Faraday Trans. 1, 1987, 83, 77.
58. (a) K. J. Rosengren, Acta Chem. Scand., 1962, 16, 1401;
59. (b) M. Kawasaki, K. Kasatani, T. Uchida and H. Sato, Chem. Lett., 1983, 325.
60. L. Lunazzi, G. Placucci and L. Grossi, J. Org. Chem., 1982, 47, 1367.
61. J. C. Scaiano and K. U. Ingold, J. Am. Chem. Soc., 1976, 98, 4727.
62. P. J. Krusic, QCPE, Program No. 210.
63. D. L. Hughes, M. Jimenez-Tenorio, G. J. Leigh, A. Houlton and J. Silver, J. Chem. Soc., Dalton Trans., 1992, 2033.
64. M. F. Hawthorne, J. Am. Chem. Soc., 1961, 83, 831.