Direct Radical Polymerization of 4-Styryldiphenylphosphine: Preparation of Cross-Linked and Non-Cross-Linked Triphenylphosphine-Containing Polystyrene Polymers

Journal of Organic Chemistry

Volumn 68, Issue 25, 2003, Pages 9831-9834

  Choi, Matthew Kwok Wai ^a   He, Helen Song ^a   Toy, Patrick H ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATION;

CROSSLINKING; POLYMERIZATION; POLYSTYRENES; SYNTHESIS (CHEMICAL);

POLYMERS;

4 STYRYLDIPHENYLPHOSPHINE; PHOSPHINE; PHOSPHINE DERIVATIVE; POLYMER; POLYSTYRENE; STYRENE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL STRUCTURE; CROSS LINKING; MITSUNOBU REACTION; POLYMERIZATION; SYNTHESIS;

EID: 0344235343     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035226+     Document Type: Article

References (50)

1. (a) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4196.
2. (b) Clapham, B.; Reger, T. S.; Janda, K. D. Tetrahedron 2001, 57, 4637-4662.
3. (c) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217-3274.
4. (d) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275-3300.
5. (e) Dickerson, T. J.; Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102, 3325-3344.
6. (f) Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345-3384.
7. (g) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385-3466.
8. Storer, R. I.; Takemoto, T.; Jackson, P. S.; Ley, S. V. Angew. Chem., Int. Ed. 2003, 42, 2521-2525.
9. (a) Cobb, J. E.; Cribbs, C. M.; Henke, B. R.; Uehling, D. E. Polystyrene. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: 1995; pp 5357-5363.
10. (b) Valentine, D. H., Jr.; Hillhouse, J. H. Synthesis 2003, 317-334.
11. For a review of polymer-supported triphenylphosphine organometallic complexes, see: Leadbeater, N. E. Curr. Med. Chem. 2002, 9, 2147-2171.
12. For applications of phosphines that contain basic functional groups to aid in chromatographic separation of the phosphine and phosphine oxide, see: Kiankarimi, M.; Lowe, R.; McCarthy, J. R.; Whitten, J. P. Tetrahedron Lett. 1999, 40, 4497-4500 and references therein.
13. For application of a phosphine that contains an acid functional group to aid in the removal of the phosphine and phosphine oxide, see: Starkey, G. W.; Parlow, J. J.; Flynn, D. L. Bioorg. Med. Chem. Lett. 1998, 8, 2385-2390.
14. For applications of phosphines that contain fluorous tags to aid in the removal of the phosphine and phosphine oxide, see: Dandapani, S.; Curran, D. P. Tetrahedron 2002, 58, 3855-3864 and references therein.
15. For application of a phosphine that contains an anthracene tag to aid in the removal of the phosphine and phosphine oxide, see: Lan, P.; Porco, J. A., Jr.; South, M. S.; Parlow, J. J. J. Comb. Chem. 2003, 5, 660-669.
16. (a) Sieber, F.; Wentworth, P. W., Jr.; Toker, J. D.; Wentworth, A. D.; Metz, W. A.; Reed, N. N.; Janda, K. D. J. Org. Chem. 1999, 64, 5188-5192.
17. (b) Kollhofer, A.; Plenio, H. Chem. Eur. J. 2003, 9, 1416-1425.
18. Arstad, E.; Barrett, A. G. M.; Hopkins, B. T.; Kobberling, J. Org. Lett. 2002, 4, 1975-1977.
19. Bergbreiter, D. E.; Li, C. Org. Lett. 2003, 5, 2445-2447.
20. For a report of this approach that contains no experimental details, see: McKinley, S. V.; Rakshys, J. W. J. Chem. Soc., Chem. Commun. 1972, 134-135.
21. Naaktgeboren, A. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1980, 102, 3350-3354.
22. Camps, F.; Castells, J.; Font, J.; Vela, F. Tetrahedron Lett. 1971, 20, 1715-1716.
23. For use of this approach to prepare non-cross-linked polystyrene-bound triphenylphosphine, see: Harrison, C. R.; Hodge, P.; Hunt, B. J.; Khoshdel, E.; Richardson, G. J. Org. Chem. 1983, 48, 3721-3728.
24. For use of this approach to prepare divinylbenzene cross-linked polystyrene-bound triphenylphosphine, see: (a) Farrall, M. J.; Frechet, J. M. J. J. Org. Chem. 1976, 41, 3877-3882.
25. (b) Bernard, M.; Ford, W. T. J. Org. Chem. 1983, 48, 326-332.
26. Relles, H. M.; Schluenz, R. W. J. Am. Chem. Soc. 1974, 96, 6469-6475.
27. Charette, A. B.; Boezio, A. A.; Janes, M. K. Org. Lett. 2000, 2, 3777-3779.
28. (a) Toy, P. H.; Janda, K. D. Acc. Chem. Res. 2000, 33, 546-554.
29. (b) Toy, P. H.; Reger, T. S.; Janda, K. D. Org. Lett. 2000, 2, 2205-2207.
30. (c) Choi, M. K. W.; Toy, P. H. Tetrahedron 2003, 59, 7171-7176.
31. (a) Toy, P. H.; Janda, K. D. Tetrahedron Lett. 1999, 40, 6329-6332.
32. (b) Toy, P. H.; Reger, T. S.; Janda, K. D. Aldrichimica Acta 2000, 33, 87-93.
33. (c) Toy, P. H.; Reger, T. S.; Garibay, P.; Garno, J. C.; Malikayil, J. A.; Liu, G.-Y.; Janda, K. D. J. Comb. Chem. 2001, 3, 117-124.
34. Borner, H. G.; Heitz, W. Macromol. Chem. Phys. 2000, 201, 740-746.
35. Hon, Y. S.; Lee, C. F.; Chen, R. J.; Szu, P. H. Tetrahedron 2001, 57, 5991-6001.
36. For an early synthesis of 1 from the simple Grignard reagent of 4-chlorostyrene in comparable yield, see: Rabinowitz, R.; Marcus, R. J. Org. Chem. 1961, 26, 4157-4158.
37. JandaJel is a registered trademark of the Aldrich Chemical Co.
38. 31P NMR spectroscopy.
39. Attempts to use benzoyl peroxide as the initiator failed to produce any filterable polymer beads.
40. A polystyrene supported ferrocene-based triarylphosphine reagent has been prepared by this method. Stille, J. K.; Su, H.; Hill, D. H.; Schneider, P. ; Tanaka, M.; Morrison, D. L.; Hegedus, L. S. Organometallics 1991, 10, 1993-2000.
41. 3/g.
42. Barrett, A. G. M.; Roberts, R. S.; Schroder, J. Org. Lett. 2000, 2, 2999-3001 and references therein.
43. Hodge, P.; Khoshdel, E. J. Chem. Soc., Perkin Trans. 1 1984, 195-198.
44. When either methanol or hexanes was used as the precipitation solvent, the polymer formed a sticky and intractable residue that was difficult to filter.
45. (a) Yaroslavsky, C.; Patchornik, A.; Katchalski, E. Tetrahedron Lett. 1970, 11, 3629-3632.
46. (b) Morawetz, H. J. Macromol. Sci. Chem. 1979, 3, 311-320.
47. (c) Alexandratos, S. D.; Miller, D. H. J. Macromolecules 1996, 29, 8025-8029.
48. (d) Deratani, A.; Darling, G. D.; Horak, D.; Frechet, J. M. J. Macromolecules 1987, 20, 767-772.
49. (e) Alexandratos, S. D.; Miller, D. H. J. Macromolecules 2000, 33, 2011-2015.
50. (f) Vaino, A. R.; Janda, K. D. J. Comb. Chem. 2000, 2, 579-596.