Spin trapping by 2-methyl-2-nitrosopropane (MNP) in the polymerization of styrene or substituted styrenes and maleic anhydride

Acta Chemica Scandinavica

Volumn 53, Issue 9, 1999, Pages 680-692

  Eberson, Lennart ^a   Persson, Ola ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004704443     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.53-0680     Document Type: Article

References (38)

1. Moad, G. and Solomon, D. H. The Chemistry of Free Radical Polymerization, Pergamon, Oxford 1995.
2. Hall, Jr., H. K. and Padias, A. B. Acc. Chem. Res. 30 (1997) 322.
3. (a) Sato, T., Hibino, K. and Otsu, T. J. Macromol. Sci.-Chem. A9 (1975) 1165;
4. (b) Sato, T., Abe, M. and Otsu, T. Makromol. Chem. 178 (1977) 1061;
5. (c) Sato, T., Abe, M. and Otsu, T. J. Makromol. Sci.-Chem. A15 (1981) 367.
6. Mash, E. A., Korth, H.-G. and DeMoss, S. M. Tetrahedron 53 (1997) 15297.
7. Eberson, L., Hartshorn, M. P. and Persson, O. J. Chem. Soc., Perkin Trans. 2 (1997) 195.
8. Sang, H., Janzen, E. G. and Poyer, J. L. J. Chem. Soc., Perkin Trans. 2 (1996) 1183. See also Eberson, L., MacCullough, J. J. and Persson, O. J. Chem. Soc., Perkin Trans. 2 (1997) 133.
9. Sang, H., Janzen, E. G. and Poyer, J. L. J. Chem. Soc., Perkin Trans. 2 (1996) 1183. See also Eberson, L., MacCullough, J. J. and Persson, O. J. Chem. Soc., Perkin Trans. 2 (1997) 133.
10. Confalone, P. N. and Huie, E. M. Org. React. (N. Y.) 36 (1988) 1.
11. For a compilation, see Eberson, L. Adv. Phys. Org. Chem. 31 (1998) 91.
12. Eberson, L. and Persson, O. Acta Chem. Scand. 52 (1998) 1081.
13. Buettner, G. R. Free Radical Biol. Med. 3 (1987) 259.
14. A rearranged Diels-Alder adduct was isolated from 1-vinylnaphthalene and maleic anhydride and shown to have initiating capability in the polymerization of methyl methacrylate. See: Sato, T., Abe, M. and Otsu, T. Makromol. Chem. 178 (1977) 1267.
15. Jonkman, L., Muller, H., Kiers, H. and Kommandeur, J. J. Phys. Chem. 74 (1970) 1650; Jonkman, L., Muller, H. and Kommandeur, J. J. Am. Chem. Soc. 93 (1971) 5833; Eberson, L., Hartshorn, M. P. and Persson, O. Acta Chem. Scand. 52 (1998) 751.
16. Jonkman, L., Muller, H., Kiers, H. and Kommandeur, J. J. Phys. Chem. 74 (1970) 1650; Jonkman, L., Muller, H. and Kommandeur, J. J. Am. Chem. Soc. 93 (1971) 5833; Eberson, L., Hartshorn, M. P. and Persson, O. Acta Chem. Scand. 52 (1998) 751.
17. Jonkman, L., Muller, H., Kiers, H. and Kommandeur, J. J. Phys. Chem. 74 (1970) 1650; Jonkman, L., Muller, H. and Kommandeur, J. J. Am. Chem. Soc. 93 (1971) 5833; Eberson, L., Hartshorn, M. P. and Persson, O. Acta Chem. Scand. 52 (1998) 751.
18. Holman, R. J. and Perkins, M. J. J. Chem. Soc. C (1971) 2324; Jacobsen, H. J. and Torssell, K. Tetrahedron Lett. (1970) 5003.
19. Holman, R. J. and Perkins, M. J. J. Chem. Soc. C (1971) 2324; Jacobsen, H. J. and Torssell, K. Tetrahedron Lett. (1970) 5003.
20. Eberson, L. and Persson, O. Unpublished results.
21. Eberson, L., Hartshorn, M. P. and Persson, O. J. Chem. Soc., Perkin Trans. 2 (1995) 1735; for a review on the use of HFP, see: Eberson, L., Hartshorn, M. P., Persson, O. and Radner, F. J. Chem. Soc., Chem. Commun. (1996) 2105.
22. Eberson, L., Hartshorn, M. P. and Persson, O. J. Chem. Soc., Perkin Trans. 2 (1995) 1735; for a review on the use of HFP, see: Eberson, L., Hartshorn, M. P., Persson, O. and Radner, F. J. Chem. Soc., Chem. Commun. (1996) 2105.
23. See, for example: Bauld, N. L., Aplin, J. T., Yueh, Endo, S. and Loving, A. J. Phys. Org. Chem. 11 (1998) 15; Aplin, J. T. and Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 (1997) 853.
24. See, for example: Bauld, N. L., Aplin, J. T., Yueh, Endo, S. and Loving, A. J. Phys. Org. Chem. 11 (1998) 15; Aplin, J. T. and Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 (1997) 853.
25. Such calculations were recently published, but the electrostatic term was neglected in spite of the fact the benzene-dichloromethane (D ≈ 5) was used as the solvent. See: Lücking, K., Rese, M. and Sustmann, R. Liebigs Ann. (1995) 1129.
26. For reviews on the application of electron transfer theory in organic chemistry, see Eberson, L. Adv. Phys. Org. Chem. 18 (1982) 79; Eberson, L. Electron Transfer Reactions in Organic Chemistry, Springer-Verlag, Heidelberg 1987.
27. For reviews on the application of electron transfer theory in organic chemistry, see Eberson, L. Adv. Phys. Org. Chem. 18 (1982) 79; Eberson, L. Electron Transfer Reactions in Organic Chemistry, Springer-Verlag, Heidelberg 1987.
28. Aurich, H. G. Can. J. Chem. 60 (1982) 1414; Aurich, H. G., Schmidt, M. and Schwerzel, T. Chem. Ber. 118 (1985) 1086; Aurich, H. G., Eidel, J. and Schmidt, M. Chem. Ber. 119 (1986) 36; Aurich, H. G. Pure Appl. Chem. 62 (1990) 183.
29. Aurich, H. G. Can. J. Chem. 60 (1982) 1414; Aurich, H. G., Schmidt, M. and Schwerzel, T. Chem. Ber. 118 (1985) 1086; Aurich, H. G., Eidel, J. and Schmidt, M. Chem. Ber. 119 (1986) 36; Aurich, H. G. Pure Appl. Chem. 62 (1990) 183.
30. Aurich, H. G. Can. J. Chem. 60 (1982) 1414; Aurich, H. G., Schmidt, M. and Schwerzel, T. Chem. Ber. 118 (1985) 1086; Aurich, H. G., Eidel, J. and Schmidt, M. Chem. Ber. 119 (1986) 36; Aurich, H. G. Pure Appl. Chem. 62 (1990) 183.
31. Aurich, H. G. Can. J. Chem. 60 (1982) 1414; Aurich, H. G., Schmidt, M. and Schwerzel, T. Chem. Ber. 118 (1985) 1086; Aurich, H. G., Eidel, J. and Schmidt, M. Chem. Ber. 119 (1986) 36; Aurich, H. G. Pure Appl. Chem. 62 (1990) 183.
32. Nelsen, S. F., Thompson-Colon, J. A., Kirste, B., Rosenhouse, A. and Kaftory, M. J. Am. Chem. Soc. 109 (1987) 7128.
33. Niki, E., Ohto, N., Kanauchi, T. and Kamiya, Y. Eur. Polym. J. 16 (1980) 559.
34. Terabe, S. and Konaka, R. J. Chem. Soc., Perkin Trans. 2 (1972) 2163.
35. Stowell, J. C. J. Org. Chem. 36 (1971) 3055.
36. Duling, D. Public EPR Software Tools, National Institute of Environmental Health Sciences, Washington 1996.
37. Schepp, N. P. and Johnston, L. J. J. Am. Chem. Soc. 118 (1996) 2872.
38. Rese, M., Dern, M., Lücking, K. and Sustmann, R. Liebigs Ann. (1995) 1139.