Selective functionalization of poly(4-methylstyrene)

Macromolecules

Volumn 30, Issue 21, 1997, Pages 6451-6457

  Sheng, Quan ^a   Stöver, Harald D H ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CERIUM COMPOUNDS; CHARGE TRANSFER; COBALT COMPOUNDS; COMPLEXATION; ELECTRONIC STRUCTURE; NITRATES; OXIDATION; POLYSTYRENES; REACTION KINETICS;

POLYMETHYLSTYRENES; STEREO ELECTRONIC EFFECTS;

METALLORGANIC POLYMERS;

EID: 0031245911     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9616625     Document Type: Article

References (52)

1. Hodge, P.; Sherrington, D. C. Polymer-Supported Reactions in Organic Syntheses; John Wiley & Sons: New York, 1980.
2. Mohanraj, S.; Ford, W. T. Macromolecules 1986, 19, 2470-2472.
3. Jones, R. G.; Matsubayashi, Y. Polymer 1990, 31, 1519-1525; 1992, 33, 1069-1072.
4. Jones, R. G.; Matsubayashi, Y. Polymer 1990, 31, 1519-1525; 1992, 33, 1069-1072.
5. Wang, H. C.; Powers, K. W. Elastomerics 1992, 124 (1), 14-19.
6. Powers, K W.; Wang, H. C.; Chung, N.-J.; Diaz, A. J.; Olkusz, J. A. U.S. Patent 5,162,445, 1992.
7. Steinke, J. H. G.; Haque, S. A.; Frechet, J. M. J.; Wang, H. C. Macromolecules 1996, 29, 6081-6089.
8. Lochmann, L.; Janata, M.; Holler, P.; Tuzar, Z.; Kratchovil, P. Macromolecules 1996, 29, 8092-8095.
9. Ferrari, L. P.; Stöver, H. D. H. Macromolecules 1991, 24, 6340-6342.
10. Stöver, H. D. H.; Li, P.; Ferrari, L.; Shaver, R.; Vlaovic, D. Polymers Having Oxidic Functionality and Derivatives Thereof. (U.S. Patent 5,376,732; Dec 27th, 1994; U.S. Patent 5,468,814, Nov 21st, 1995).
11. Shaver, R. T.; Vlaovic, D.; Reviakine, I.; Wittaker, R.; Ferrari, L. P.; Stöver, H. D. H.; J. Polym. Sci., Polym. Chem. 1995, 33, 957-965
12. Hay, A. S.; Blanchard, H. S. Can. J. Chem. 1965, 43, 1306-1317.
13. Brill, W. F. Ind. Eng. Chem. 1960, 10, 837-840.
14. Raghavendrachar, P.; Ramachandran, S. Ind. Eng. Chem. Res. 1992, 31, 453-462.
15. Syper, L.; Tetrahedron Lett. 1966, 4493.
16. Andrulis, P. J.; Dewar, M. J. S.; Dietz, R.; Hunt, R. L. J. Am. Chem. Soc. 1966, 88, 5473-5478.
17. Trahanovsky, W. S.; Young, L. B.; J. Org. Chem., 1966, 31, 2033-2035.
18. Sakota, K.; Kamiya, Y.; Ohta, N. Can. J. Chem., 1969, 47, 387-392.
19. Heiba, E. I.; Dessau, R. M.; Koehl, W. R. J. Am. Chem. Soc. 1969, 91, 6830-6837.
20. Onopchenko, A.; Schulz, J. G. D. J. Org. Chem. 1972, 37, 2564-2566.
21. Onpchenko, A.; Schulz, J. G. D.; Seekircher, R.; J. Org. Chem. 1972, 37, 1414-1417.
22. Lande, S. S.; Falk, C. D.; Kochi, J. K. J. Inorg. Nucl. Chem. 1971, 33, 4101-4109.
23. In the reactions involving the nonpolar cosolvents benzene or n-heptane, only a small fraction of the CAN dissolved to give the solution a yellow color. This color diminished during these reactions, and the solid CAN portion changed color from orange to light yellow or even white. In the reactions involving the more polar cosolvents methyl ethyl ketone and diethylene glycol dimethyl ether, the CAN was substantially soluble. These solutions were hence intensely yellow at the outset and changed to light orange during the reactions.
24. Weir, N. A.; Milkie, T. H. Polym. Degrad. Stab. 1980, 2, 225-238.
25. Boerio, F. J.; Tsai, W. H.; Hong, P. P.; Montaudo, G. Macromolecules 1989, 22, 3955-3960.
26. Dust, L. A.; Gill, E. W. J. Chem. Soc. C 1979, 1630-1631.
27. Baciocchi, E.; Rol, C.; Mandolini, L. J. Org. Chem. 1977, 42, 3682-3686.
28. Baciocchi, E.; Mandolini, L.; Rol, C. J. Org. Chem. 1980, 45, 3906-3909.
29. Wiberg, K. B. Oxidation in Organic Chemistry, Part A; Academic Press: New York, 1965; p 271.
30. Preliminary, unpublished results cited by: Martin, T. W.; Burk, J. M.; Henshell, A. J. Am. Chem. Soc. 1966, 88, 1097.
31. Trahanovsky, W. S.; Cramer, J. J. Org. Chem. 1971, 36, 1890-1893.
32. Baciocchi, E.; Mandolini, L.; Rol, C. J. Am. Chem. Soc. 1980, 102, 7597-7599.
33. Baciocchi, E.; Ruzziconi, R. J. Chem. Soc., Chem. Commun., 1984, 445-446.
34. Baciocchi, E.; Eberson, L.; Rol, C. J. Org. Chem. 1982, 47, 5106-5110.
35. Baciocchi, E.; Dalla Court, A.; Eberson, L.; Mandolini, L.; Rol, C. J. Org. Chem. 1986, 51, 4544-4548.
36. Baciocchi, E.; Mattioli, M.; Romano, R.; Ruzziconi, R. J. Org. Chem. 1991, 56, 7154-7160.
37. Baciocchi, E.; Rol, C.; Ruzziconi, R. J. Chem. Res. Synop. 1984, 334-335.
38. Shono, T.; Matsumura, Y. J. Org. Chem. 1970, 35, 4157.
39. Ingold, K. U. Pure Appl. Chem. 1967, 15, 49-67.
40. Pritzkow, W.; Thomas, G.; Willecke, L. J. Prakt. Chem. 1985, 847-851.
41. Kamiya, Y.; Kashima, M. Bull. Chem. Soc. Jpn. 1973, 46, 905-908.
42. Hendriks, C. F.; Van Beek, H. C. A.; Heertjes, P. M. Ind. Eng. Chem. Prod. Res. Dev. 1978, 17, 256-260.
43. For diphenylethane the expected side chain acetoxylation products were obtained. For diphenyltetramethylethane, on the other hand, no reaction was observed, presumably due to the absence of benzylic hydrogen.
44. Hanotier, J.; Hanotier-Bridoux, M. J. Chem. Soc., Perkin Trans. 2 1973, 1035-1039.
45. Eberson, L.; Jonsson, L.; Wistrand, L.-G. Acta Chim. Scand., B 1978, 32, 520-530.
46. Fréchet, J. M. J.; Matuszczak, S.; Reck, B.; Stöver, H. D. H.; Willson, C. G.; Macromolecules 1991, 24, 1746.
47. 2] the rate of oxidation increased approximately linearly with acetic acid volume fraction. No attempt was made to study the effects of the cosolvent ratio in this work.
48. 16
49. Hanotier, J.; Hanotier-Bridoux, M.; de Radzitky, P. J. Chem. Soc., Perkin Trans. 2, 1973, 381-386.
50. This corresponds to a yield based on cobalt(III) acetate of only 25%, well below the 70-80% yield based on CAN described above. However, it is possible that longer reaction times (Table 8) might increase conversion and yield.
51. Third entry, Table 8.
52. It is unlikely that backbone cleavage and polymer-polymer coupling (through radical combination or Friedel-Crafts alkylation) just balance to give constant MW, as the molecular weights were not sensitive to Co(III) concentration or to reaction time. At least the radical combination route would be sensitive to such changes of conditions.