α,ω-difunctional perfluorinated spacer arms for polymeric material derivatization

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 408-412

  Mougenot, Patrick ^a,b   Mertens, Paul ^a,b   Nguyen, Muriel ^a,b   Touillaux, Roland ^a,c   Marchand Brynaert, Jacqueline ^a,b  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b Lab de Chim Organique de Synt

^c Lab de Chim Phys et Cristal

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003053822     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951248n     Document Type: Article

References (55)

1. (a) Hudlicky, M. Chemistry of Organic Fluorine Compounds; Ellis Horwood Ltd.: Chichester, 1992.
2. (b) Welch, J. T. Selective Fluorination in Organic and Bioorganic Chemistry; ACS Symposium Series 456; American Chemical Society: Washington, DC, 1991.
3. (a) Filler, A.; Kobayashi, Y. Biomedical Aspects of Fluorine Chemistry; Elsevier Biomedical Press: Amsterdam, 1982.
4. (b) Welch, J. T.; Eswarakrischnan, S. Fluorine in Bioorganic Chemistry; J. Wiley and Sons: New York, 1991.
5. (a) Fielding, H C. In Organofluorine Chemicals and their Industrial Applications; Banks, R. E., Ed.; Ellis Horwood Ltd.: Chichester, 1979; p 214.
6. (b) Smith, S. In Preparation, Properties and Industrial Applications of Organofluorine Compounds; Banks, R. E., Ed.; Ellis Horwood Ltd.: Chichester, 1982; p 235.
7. (a) Kato, M.; Takakura, T.; Yamabe, M.; Okano, T.; Kataoka, K.; Sakurai, Y.; Imachi, K.; Atsumi, K. Prog. Artif. Organs 1983, 2, 858.
8. (b) Boutevin, B.; Robin, J. J. Adv. Polym. Sci. 1992, 102, 105.
9. Taguchi, V. Y. In Gas Chromatography: Biochemical, Biomedical and Clinical Applications; Clement, R. E., Ed.; J. Wiley and Sons: New York, 1990; p 129.
10. (a) Loccufier, J.; Van Bos, M.; Schacht, E. Polym. Bull. 1991, 27, 201.
11. (b) Chilkoti, A.; Ratner, B. D. Surface Interface Anal. 1991, 17, 567.
12. Deldime, M ; Dewez, J.-L.; Schneider, Y.-J.; Marchand-Brynaert, J. Appl. Surf. Sci. 1995, 90, 1.
13. (a) Marchand-Brynaert, J.; Deldime, M.; Dupont, I.; Dewez, J.-L.; Schneider, Y.-J. J. Colloid Interface Sci. 1995, 173, 236.
14. (b) Mougenot, P.; Koch, M.; Dupont, I.; Schneider, Y.-J.; Marchand-Brynaert, J. J. Colloid Interface Sci. 1996, in press.
15. (a) Reilley, C. N.; Everhart, D. S.; Ho, F. F. L. In Applied Electron Spectroscopy for Chemical Analysis; Windawi, H., Ho, F. F. L , Eds.; J. Wiley and Sons: New York, 1982; Chapter 6.
16. (b) Clark, D. R. Pure Appl. Chem. 1982, 54, 415.
17. (a) Batich, C. D.; Wendt, R. C. Chemical Labels to Distinguish Surface Functional Groups Using X-Ray Photoelectron Spectroscopy (ESCA); ACS Symposium Series 162; American Chemical Society: Washington, DC, 1981; pp 221-235.
18. (b) Everhart, D. S.; Reilley, C. N. Anal. Chem. 1981, 53, 665.
19. (c) Chilkoti, A.; Ratner, B. D.; Briggs, D. Chem. Mater. 1991, 3, 51.
20. (d) Ameen, A. P.; Ward, R. J.; Short, R. D.; Beamson, G.; Briggs, D. Polymer 1993, 34, 1795.
21. Piglowski, J.; Gancarz, I.; Staniszewska-Kus, J.; Paluch, D.; Szymonowicz, M.; Konieczny, A. Biomaterials 1994, 15, 909.
22. (a) Ward, R. B. J. Org. Chem. 1965, 30, 3009.
23. (b) Mc Bee, E. T.; Marzluff, W. F.; Pierce, O. R. J. Am. Chem. Soc. 1952, 74, 444
24. (a) Xu, Y., Jin, F.; Huang, W. J. Org. Chem. 1994, 59, 2638.
25. (b) Mc Clinton, M. A. ; Mc Clinton, D. A. Tetrahedron 1992, 48, 6555.
26. (c) Boivin, J.; El Kaim, L.; Zard, S. Z. Tetrahedron 1995, 51, 2573.
27. (d) Okano, T.; Takakura, N.; Nakano, Y.; Okajima, A.; Eguchi, S. Tetrahedron 1995, 51, 1903.
28. (a) Baum, K.; Malik, A. A. J. Org. Chem. 1994, 59, 6804.
29. (b) Urata, H.; Kinoshita, Y.; Asanuma, T.; Kosukegawa, O.; Fuchikami, T. J. Org. Chem. 1991, 56, 4996.
30. (c) Qiu, Z.-M.; Burton, D. J. J. Org. Chem. 1995, 60, 3465.
31. (a) Henne, A. L.; Francis, W. C. J. Am. Chem. Soc. 1953, 75, 991.
32. (b) Haszeldine, R. N. J. Chem. Soc. 1953, 1757.
33. (c) Henne, A. L.; Pelley, R. L. J. Am. Chem. Soc. 1952, 74, 1426.
34. (a) O'Hagan, D.; Zaidi, N. A.; Lamont, R. B. Tetrahedron: Asymmetry 1993, 4, 1703.
35. (b) Budovskaya, L. D.; Ivanova, V. N.; Gol'tsin, B. E.; Solov'eva, N. P. Gotlib, Y. Y. Kinet. Katal. 1978, 19, 1325.
36. (c) Montanari, V.; Quici, S.; Resnati, G. Tetrahedron Lett. 1994, 35, 1941.
37. (a) Hung, M.-H.; Rozen, S.; Smart, B. E. J. Org. Chem. 1994, 59, 4332.
38. (b) Patel, N. R.; Chen, J.; Zhang, Y. F.; Kirchrmier, R. L.; Shreeve, J. M. Inorg. Chem. 1994, 33, 5463.
39. (c) Heilmann, S. M.; Drita, G. J.; Janulis, E. R.; Krepski, L. R.; Rasmussen, J. K.; Babirad, S. A.; Moren, D. M.; Bonham, D. S.; Pathre, S. V.; Greening, G. W J. Fluorine Chem. 1992, 59, 387.
40. (d) Farnham, W. B.; Roe, D. C.; Dixon, D. A.; Calabrese, J. C.; Harlow, R. L. J. Am. Chem. Soc. 1990, 112, 7707.
41. Meinert, H.; Geister, U. J. Fluorine Chem. 1994, 68, 221.
42. Baldwin, J. E.; Adlington, R. M.; Birch, D. J. Tetrahedron Lett. 1985, 26, 5931.
43. (a) Wiley, G. A.; Hershkowitz, R. L.; Rein, B. M.; Chung, B. C. J. Am. Chem. Soc. 1964, 86, 964.
44. (b) Hrubiec, R. T.; Smith, M. B. J. Org. Chem. 1984, 49, 431.
45. (a) Pirkle, W. H.; Hauske, J. R.; Eckert, C. A.; Scott, B. A. J. Org. Chem. 1977, 42, 3101.
46. (b) Bordwell, F. G.; Branner, Jr., W. T. J. Am. Chem. Soc. 1964, 86, 4645.
47. (c) Mc Bee, E. T.; Campbell, D. H.; Roberts, C. W. J. Am. Chem. Soc. 1955, 77, 3149.
48. (d) Tiers, G. V. D.; Brown, H. A.; Reid, T. S. J. Am. Chem. Soc. 1953, 75, 5978.
49. (a) Ohta, Y.; Kohda, K.; Kimoto, H.; Okano, T.; Kawazoc, Y. Chem. Pharm. Bull. 1988, 36, 2410.
50. (b) Burdon, J.; Mc Loughlin, V. C. R. Tetrahedron 1965, 21, 1.
51. Loupy, A.; Philippon, N ; Pigeon, N.; Sansoulet, J.; Galons, H. Synth. Commun. 1990, 20, 2855.
52. Bodansky, M.; Bodansky, A. The Practice of Peptide Synthesis, 2nd ed., Springer-Verlag: Berlin, 1994.
53. Richter, R.; Ulrich, H. In Chemistry of Cyanates and Isocyanates; Patai, S., Ed.; J. Wiley and Sons: New York, 1977; p 619.
54. (a) Stinson, S. Chem Eng. 1995, April 17, 23.
55. (b) Santaella, C.; Vierling, P.; Riess, J. G. New J. Chem. 1991, 15, 685.