Selectivity of the Reaction of Free Radicals with Styrene

Macromolecules

Volumn 15, Issue 3, 1982, Pages 909-914

  Moad, Graeme ^a   Rizzardo, Ezio ^a   Solomon, David H ^a  

^a CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000610722     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/ma00231a042     Document Type: Article

References (46)

1. Bevington, J. C.; Ebdon, J. R. In “Developments in Polymerization”; Applied Science Publishers: London, 1979; pp 1–43.
2. Minisci, F.; Citterio, A. Adv. Free Radical Chem. 1980, 6, 65–153.
3. Rüchardt, C. Top. Curr. Chem. 1980, 88, 1–32.
4. Tedder, J. M.; Walton, J. C. Tetrahedron 1980, 36, 701–707.
5. Moad, G.; Rizzardo, E.; Solomon, D. H. J. Macromol. Sci., Chem. 1982, 17, 51–59 (this work was presented at the 11th Australian Polymer Symposium, Lome, 1980).
6. Rizzardo, E.; Solomon, D. H. Polym. Bull. 1979, 1, 529–534.
7. Griffiths, P. G.; Rizzardo, E.; Solomon, D. H. J. Macromol. Sci., Chem. 1982, 17, 45–50.
8. Aleksandrov, A. L.; Pliss, E. M.; Shuvalov, V. F. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transi.) 1979, 28, 2262–2267.
9. Schmid, P.; Ingold, K. U. J. Am. Chem. Soc. 1978, 100, 2493–2500.
10. Golubev, V. A.; Zhdanov, R. I.; Rozantsev, E. G. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1970, 186–187.
11. Golubev, V. A.; Zhdanov, R. I.; Protsishin, I. T.; Rozantsev, E. G. Dokl. Phys. Chem. (Engl. Transl.) 1970, 195, 952–955.
12. Bartlett, P. D.; Benzing, E. P.; Pincock, R. E. J. Am. Chem. Soc. 1960, 82, 1762–1768.
13. Hocking, M. B. Can. J. Chem. 1974, 52, 2730–2735.
14. Kato, M.; Kamogawa, H. J. Polym. Sci., Polym. Chem. Ed. 1966, 4, 1773–1782.
15. Dale, W. J.; Hennis, H. E. J. Am. Chem. Soc. 1958, 80, 3645–3649.
16. Huber, W. F.; Renoll, M.; Rossow, A. G.; Mowry, D. T. J. Am. Chem. Soc. 1946, 68, 1109–1112.
17. Buquet, A.; Couture, A.; Lablache-Combier, A. J. Org. Chem. 1979, 44, 2300–2303.
18. Gratten, D. W.; Carlsson, D. J.; Howard, J. A.; Wiles, D. H. Can. J. Chem. 1979, 57, 2834–2842.
19. Scott, A. C.; Tedder, J. M.; Walton, J. C.; Mhatre, S. J. Chem. Soc., Perkin Trans. 2 1980, 260–266.
20. Moad, G.; Rizzardo, E.; Solomon, D. H. Tetrahedron Lett. 1981, 22, 1165–1168.
21. Nitroso compounds are well-known to be reactive toward olefins (see, for example: Shenk, C.; DeBoer, Th. J. Tetrahedron 1979, 35, 147–153.
22. Motherwell, W. B.; Roberts, J. S. J. Chem. Soc., Chem. Commun. 1972, 329–330) and can be excellent radical scavengers (see ref 9).
23. The ratio [21 + 22]:[6] decreases slightly with nitroxide concentration ≤0.01 M. While this variation is within experimental error, a possible explanation for the observed trend is that the radical 26 can be converted into 25 by a 1,2-benzoyloxy group migration (Beckwith, A. L. J.; Thomas, C. B. J. Chem. Soc., Perkin Trans. 2 1973, 861–872).
24. Moad, G.; Solomon, D. H.; Johns, S. R.; Willing, R. I. Macromolecules, in press.
25. Bevington, J. C.; Jemmett, J. A. L. J. Chem. Soc., Faraday Trans. 1 1973, 69, 1866–1871.
26. Bevington, J. C.; Brooks, C. S. J. Polym. Sci. 1956, 22, 257–261.
27. Singh, H.; Tedder, J. M. J. Chem. Soc., Chem. Commun. 1981, 70–71.
28. Moad, G.; Rizzardo, E.; Solomon, D. H. Polym. Bull., in press.
29. Brokenshare, L.; Ingold, K. U. Int. J. Chem. Kinet. 1981, 3, 343–357.
30. Arshady, R.; Kenner, G. W.; Ledwith, A. J. J. Polym. Sci., Polym. Chem. Ed. 1974, 12, 2017–2025.
31. Kern, W.; Hertz, W.; Jager, M.; Pfitzner, K.; Wirth, H. O. Makromol. Chem. 1969, 126, 73–86.
32. Kurz, M. E.; Pellegrini, M. J. Org. Chem. 1970, 35, 990–992.
33. Nakata, T.; Tokumaru, K.; Simamura, O. Tetrahedron Lett. 1967, 3303–3308.
34. Chalfont, G. R.; Hey, D. H.; Liang, K. S. Y.; Perkins, M. J. J. Chem. Soc. B 1971, 233–245.
35. Porta, O. Chim. Ind. (Milan) 1980, 62, 119–127.
36. Perkins, M. J. In “Free Radicals”; Kochi, J. K., Ed.; Wiley-Interscience: New York, 1973; Vol. 2, pp 231–271.
37. It is known that benzoyloxy radicals react with polystyrene to give a mixture of aromatic and aliphatic benzoate esters (Haas, H. C. J. Polym. Sci. 1961, 54, 287–299).
38. Bellus, D.; Slama, P.; Hrdkovic, P.; Manasek, Z.; Durisinova, L. J. Polym. Sci., Part C 1969, 22, 629–643.
39. Suzuki, H.; Tanaka, Y.; Ishii, Y. Sen'i Gakkaishi 1979, 35, T296–302.
40. o-Hydroxybenzophenone derivatives are sometimes incorporated purposely into polystyrene to enhance its photostability (McKellar, J. F.; Allen, N. F. “Photochemistry of Man-Made Polymers”; Applied Science Publishers: London, 1978; Chapter 5, pp 216–255).
41. 1/2 (350 °C) = 2.5 and 37 min, respectively (Taylor, R.; Smith, G. G.; Wetzel, W. H. J. Am. Chem. Soc. 1962, 84, 4817–4824).
42. Data for the corresponding benzoates are not available but benzoate esters are known to be generally less stable than the corresponding acetates (Taylor, R. J. Chem. Soc., Perkin Trans. 2 1975, 1025–1029).
43. Singh, M.; Nandi, U. S. J. Polym. Sci., Polym. Lett. Ed. 1979, 17, 121–124.
44. Jellineck, H. H. G. In “Styrene”; Boundy, R. H., Boyer, R. F., Eds.; Reinhold: New York, 1952; p 649.
45. Cameron, G. C.; McWalter, I. T. Macromolecules 1978, 11, 696–700.
46. Rudin, A.; Samanta, M. C.; Reilly, P. M. J. Appl. Polym. Sci. 1979, 24, 171–185.