Functional Polymers from (Vinyl)polystyrene. Short Routes to Binding Functional Groups to Polystyrene Resin through a Dimethylene Spacer: Bromine, Sulfur, Phosphorus, Silicon, Hydrogen, Boron, and Oxygen

Journal of Organic Chemistry

Volumn 62, Issue 26, 1997, Pages 8987-8993

  Stranix, Brent R ^a   Gao, Jian Ping ^a   Barghi, Roya ^a   Salha, Jean ^a   Darling, Graham D ^b  

^a MCGILL UNIVERSITY   (Canada)

^b Active Materials Inc   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000096948     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960406n     Document Type: Article

References (77)

1. Ford, W. T. Polymeric Reagents and Catalysts; American Chemical Society: Washington, DC, 1986; Vol. 308.
2. Akelah, A.; Moet, A. Functionalized Polymers and Their Applications; Chapman and Hall: New York, 1990.
3. Soutif, J.-C.; Brosse, J.-C. React. Polym. 1990, 12, 3-29.
4. Sherrington, D. C.; Hodge, P. Syntheses and Separations Using Functional Polymers; John Wiley & Sons: Toronto, 1988.
5. Takemoto, K.; Inaki, Y.; Ottenbrite, R. M. Functional Monomers and Polymers: Procedures, Synthesis, Applications; Marcel Dekker: New York, 1987.
6. Guyot, A. In Syntheses and Separations Using Functional Polymers; Sherrington, D. C., Hodge, P., Eds.; John Wiley & Sons: Toronto, 1988; p 1-42.
7. Deratani, A.; Darling, G. D.; Fréchet, J. M. J. Polymer 1987, 28, 825-830.
8. Deratani, A.; Maraldo, T.; Darling, G. D.; Fréchet, J. M. J. React. Polym. 1988, 9, 19-28.
9. Stranix, B. R.; Darling, G. D. Biotechnol. Tech. 1995, 9, 75-80.
10. Ford, W. T. In Polymeric Reagents and Catalysts; Ford, W. T., Ed.; American Chemical Society: Washington, DC, 1986; Vol. 308, pp 247-285.
11. Brunelet, T.; Bartholin, M.; Guyot, A. Angew. Makromol. Chem. 1982, 106, 79-90.
12. Guyot, A. React. Polym. 1989, 10, 113-129.
13. Fréchet, J. M. J. In Chemistry of Crosslinked Polymers; Labana, S. S., Ed.; Academic Press: New York, 1977; p 59.
14. Akelah, A.; Sherrington, D. C. Chem. Rev. 1981, 82, 557.
15. O'Brien, R. A.; Chen, T.; Rieke, R. D. J. Org. Chem. 1992, 57, 2667-2677.
16. Darling, G. D.; Fréchet, J. M. J. J. Org. Chem. 1986, 51, 2270-2276.
17. Darling, G. D.; Fréchet, J. M. J. In Chemical Reactions on Polymers; Benham, J. L., Kinstle, J. F., Eds.; American Chemical Society: Washington, DC, 1988; Vol. 364, pp 24-36.
18. Gao, J. P.; Barghi, R.; Darling, G. D. Book of Abstracts, 33rd IUPAC International Symposium on Macro molecules, Montreal, QC, Canada, July 8-13, 1990; International Union of Pure and Applied Chemistry, 1990; Session 1.7.5.
19. Hodge, P. In Syntheses and Separations Using Functional Polymers; Sherrington, D. C., Hodge, P., Eds.; Wiley: Chichester, 1988; pp 43-122.
20. Hodge, P. In Encyclopedia of Polymer Science and Engineering; Mark, H. F., Ed.; John Wiley & Sons: Toronto, 1988; Vol. 12, pp 622-658.
21. Vogl, O. J. Macromol. Sci., Chem. 1984, 21, 1217.
22. Albright, R. L. React. Polym. 1986, 4, 155-174.
23. Jacobelli, H.; Bartholin, M.; Guyot, A. J. Appl. Polym. Sci. 1979, 23, 927.
24. Shea, K. J.; Susuki, D. Y.; Stoddard, G. J. Macromolecules 1989, 22, 1722-1730.
25. Malinski, J.; Klaban, J.; Dusek, K. J. Macromol. Sci., Chem. 1971, 5, 1071-1085.
26. Kwant, P. W. J. Polym. Sci., Polym. Chem. Ed. 1979, 17, 1331.
27. Periyasamy, M.; Ford, W. T.; McEnroe, F. J. J. Polym. Sci., Polym. Chem. Ed. 1989, 27, 2357-2366.
28. Gao, J. P.; Morin, F. G.; Darling, G. D. Macromolecules 1993, 26, 1196-1198.
29. Bartholin, M.; Boissier, G.; Dubois, J. Makromol. Chem. 1981, 182, 2075-2085.
30. Okubo, M.; Nakagawa, T. Colloid Polym. Sci. 1992, 270, 853-858.
31. Smets, G.; Hoovers, J.; van Humbeck, W. J. Appl. Polym. Sci. 1961, 5, 149.
32. Walling, C.; Huyser, E. S. Org. React. 1963, 13, 91-149.
33. Farrell, M. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1978, 100, 7998.
34. Szabó, L. F.; Tétényi, P., Jr.; Pecher, J. React. Polym. 1989, 11, 47-56.
35. Faber, M. C.; van de Berg, H. J.; Challa, G.; Pandit, U. K. React. Polym. 1988, 11, 117-126.
36. Stranix, B. R.; Darling, G. D., manuscript in preparation for J. Org. Chem.
37. Fréchet, J. M. J.; Eichler, E. Polym. Bull. 1982, 7, 345.
38. Neumann, W. P.; Peterseim, M. React. Polym. 1993, 20, 189-205.
39. Bootsma, J. P. C.; Eling, B.; Challa, G. React. Polym. 1984, 3, 17.
40. Schutten, J. H.; Hastenberg, C. H. v.; Diet, P.; German, A. L. Angew. Makromol. Chem. 1980, 89.
41. Funke, W. J. Oil Colour Chem. Assoc. 1977, 60, 438.
42. Kharasch, M. S.; Engelmann, R.; May, G. L. J. Org. Chem 1937, 2, 288.
43. Hey, D. H.; Waters, W. A. Chem. Rev. 1937, 21, 169.
44. Stacey, F. W.; Harris Jr., J. F. Org. React. 1963, 13, 150-376.
45. Farrall, M. J.; Fréchet, J. M. J. J. Org. Chem. 1976, 41, 3877-3882.
46. Société des usines chimiques Rhône-Poulenc Br. Patent 438 820, 1935; Chem. Abstr. 1936, 30, 2993.
47. Société des usines chimiques Rhône-Poulenc Br. Patent 438 820, 1935; Chem. Abstr. 1936, 30, 2993.
48. Walling, C.; Kharasch, M. S.; Mayo, F. R. J. Am. Chem. Soc. 1939, 61, 2693-2696.
49. Thaler, W. A. Methods Free-Radical Chem. 1969, 2, 121-227, 182-195.
50. Davies, J. A.; Sood, A. Makromol. Chem., Rapid Commun. 1983, 4, 777.
51. Crosby, G. A. U.S. Patent 3 928 293, 1974; Chem. Abstr. 1975, 84, 106499u.
52. Crosby, G. A. U.S. Patent 3 928 293, 1974; Chem. Abstr. 1975, 84, 106499u.
53. Svirskaya, P. I.; Leznoff, C. C. J. Org. Chem. 1987, 52, 1362-1364.
54. Parrish, J. R. Chem. Ind. (London) 1956, 137.
55. Boutevin, B.; Fleury, E.; Parisi, J. P.; Pietrasanta, Y. Macromol. Chem. Phys. 1989, 190, 2363-2372.
56. Jacobine, A. F.; Glaser, D. M.; Nakos, S. T. In Radiation Curing of Polymer Materials.; Hoyle, C. E., Kinstle, J. F., Eds.; American Chemical Society: Washington, D C, 1990; pp 160-175.
57. Fyles, T. M.; Leznoff, C. C.; Weatherston, J. Can. J. Chem. 1978, 56, 1031.
58. Morse, B. K.; Tarbell, D. S. J. Am. Chem. Soc. 1952, 74, 416-419.
59. Showell, J. S.; Russell, J. R.; Swern, D. J. Org. Chem. 1962, 27, 2853-2858.
60. Hodge, P.; Waterhouse, J. J. Chem. Soc., Perkin Trans. 1 1983, 2319.
61. Leznoff, C. C.; Synawyk, W. J. Org. Chem. 1977, 42, 3203.
62. Garrou, P. E. In Polymeric Reagents and Catalysts; Ford, W. T., Ed.; American Chemical Society: Washington, DC, 1986; Vol. 308, pp 84-106.
63. Amaratunga, W.; Fréchet, J. M. J. Polym. Prepr. 1981, 22, 151.
64. Verkade, J. G.; Quin, L. D. Phosphorous-31 NMR Spectroscopy in Stereochemical Analysis; VCH Publishers: New York, 1987; Vol. 8.
65. Alexandratos, S. D.; Quillen, D. R. React. Polym. 1990, 12, 255-265.
66. Sundell, M. J., Nasman, J. H. Chemtech 1993, 16-23.
67. Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307-1309.
68. Chan, T. H.; Huang, W. Q. J. Chem. Soc., Chem. Commun. 1985, 909-912.
69. Fréchet, J. M. J.; Darling, G. D.; Itsuno, S.; Lu, P. Z.; Vivas de Meftahi, M.; Rolls Jr., W. A. Pure Appl. Chem. 1988, 60, 353-364.
70. Stover, H.; Lu, D. H.; Zhi, P.; Fréchet, J. M. Polymer Bull. 1991, 575-582.
71. Voorhoeve, R. J. H. Organohalosilanes: Precursors to Silicones; Elsevier Publishing Company: New York, 1967.
72. Lewis, L. N.; Lewis, N.; Uriarte, R. J. In Homogeneous Transition Metal Catalyzed Reactions; Moser, W. R., Slocum, D. W., Eds.; American Chemical Society: Washington, DC, 1992; Vol. 230, pp 541-549.
73. Stranix, B. R.; Liu, H. Q.; Darling, G. D. J. Org. Chem. 1997, 62, 6183-6186.
74. Loim, N. M. Synthesis 1974, 633-651.
75. Brown, H. C.; Zweifel J. Am. Chem. Soc. 1960, 82, 4708.
76. Srebnik, M.; Cole, T. E.; Brown, H. C. J. Org. Chem. 1990, 55, 5051-5058.
77. Budesinsky, B. Anal. Chem. 1965, 9, 1159.