New sterically hindered nitroxides for the living free radical polymerization: X-ray structure of an α-H-bearing nitroxide

Macromolecules

Volumn 37, Issue 1, 2004, Pages 27-34

  Studer, Armido ^a   Harms, Klaus ^a   Knoop, Christoph ^a   Müller, Christoph ^a   Schulte, Tobias ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; AMINES; BLOCK COPOLYMERS; CHEMICAL BONDS; DECOMPOSITION; INFRARED SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYSTYRENES; REACTION KINETICS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

ALKOXYAMINE; HOMOLYSIS; LIVING FREE RADICAL POLYMERIZATION; NITROXIDES; POLYDISPERSITY;

FREE RADICAL POLYMERIZATION;

EID: 1642496779     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma035128q     Document Type: Article

References (37)

1. (a) Solomon, D. H.; Rizzardo, E.; Cacioli, P. US Patent 4,581,429; P. Eur. Pat. Appl. 135280 (Chem. Abstr. 1985, 102, 221335q).
2. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987.
3. (c) Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661.
4. (a) Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921.
5. (b) Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101, 3689.
6. Rizzardo, E.; Chiefari, J.; Mayadunne, R. T. A.; Moad, G.; Thang, S. H. In Controlled/Living Radical Polymerization, Matyjaszewski, K., Ed.; American Chemical Society: Washington, DC, 2000; ACS Symposium Series 768, p 278.
7. Fischer, H. Chem. Rev. 2001, 101, 3581.
8. Grimaldi, S.; Finet, J.-P.; Le Moine, F.; Zeghdaoui, A.; Tordo, P.; Benoit, D.; Fontanille, M.; Gnanou, Y. Macromolecules 2000, 33, 1141.
9. Le Mercier, C.; Acerbis, S.; Bertin, D.; Chauvin, F.; Gigmes, D.; Guerret, O.; Lansalot, M.; Marque, S.; Le Moigne, F.; Fischer, H.; Tordo, P. Macromol. Symp. 2002, 182, 225.
10. Benoit, D.; Chaplinski, V.; Braslau, R.; Hawker, C. J. J. Am. Chem. Soc. 1999, 121, 3904.
11. For an X-ray structure of a similar nitroxide see: Reznikov, V. A.; Gutorov, I. A.; Gatilov, Y. V.; Rybalova, T. V.; Volodarsky, L. B. Russ. Chem. Bull. 1996, 45, 384. For an X-ray structure of an SG1 type nitroxide see ref 6.
12. For an X-ray structure of an alkoxyamine derived from 2 see: Bosman, A. W.; Vestberg, R.; Heumann, A.; Fréchet, J. M. J.; Hawker, C. J. J. Am. Chem. Soc. 2003, 125, 715.
13. Brimacombe, J. S. B.; Rahman, K. M. M. J. Chem. Soc., Perkin Trans. 1 1985, 1067.
14. Maguire, A. R.; Buckley, N. R.; O'Leary, P.; Ferguson, G. J. Chem. Soc., Perkin Trans. 1 1998, 4077.
15. Corey, E. J.; Gross, A. W. Org. Synth. 1987, 65, 166.
16. Newkome, G. R.; Behera, R. K.; Moorefield, C. N.; Baker, G. R. J. Org. Chem. 1991, 56, 7162.
17. Matyjaszewski, K.; Woodworth, B. E.; Zhang, X.; Gaynor, S. G.; Metzner, Z. Macromolecules 1998, 31, 5955.
18. For a similar approach for the formation of an Alkoxyamine initiator, see: Zink, M.-O.; Kramer, A.; Nesvadba, P. Macromolecules 2000, 33, 8106.
19. Radical styrene polymerization in the presence of nitroso-tert-octane has been reported: Catala, J.-M.; Jousset, S.; Lamps, J.-P. Macromolecules 2001, 34, 8654.
20. (a) Benoit, D.; Hawker, C. J.; Huang, E. E.; Lin, Z.; Russell, T. P. Macromolecules 2000, 33, 1505.
21. (b) Benoit, D.; Grimaldi, S.; Robin, S.; Finet, J.-P.; Tordo, P.; Gnanou, Y. J. Am. Chem. Soc. 2000, 122, 5929.
22. (c) Lacroix-Desmazes, P.; Lutz, J.-F.; Chauvin, F.; Severac, R.; Boutevin, B. Macromolecules 2001, 34, 8866.
23. (d) Souaille, M.; Fischer, H. Macromolecules 2002, 35, 248.
24. (e) Tang, C.; Kowalewski, T.; Matyjaszewski, K. Macromolecules 2003, 36, 1465.
25. Marque, S.; LeMercier, C.; Tordo, P.; Fischer, H. Macromolecules 2000, 33, 4403.
26. Marque, S.; Fischer, H.; Baier, E.; Studer, A. J. Org. Chem. 2001, 66, 1146.
27. Schulte, T.; Studer, A. Macromolecules 2003, 36, 3078.
28. (a) Kovtun, G. A.; Aleksandrov, A. L.; Golubev, V. A. Bull. Acad. Chim. USSR, Div. Chem. 1974, 10, 2115.
29. (b) Howard, J. A.; Tait, J. C. J. Org. Chem. 1978, 43, 4279.
30. (c) Grattan, D. W.; Carlsson, D. J.; Howard, J. A.; Wiles, D. M. Can. J. Chem. 1979, 57, 2834.
31. Gennady, S.; Ananchenko, G. S.; Fischer, H. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 3604.
32. Goto, A.; Kwak, Y.; Yoshikawa, C.; Tsujii, Y.; Sugiura, Y.; Fukuda, T. Macromolecules 2002, 35, 3520.
33. Bowman, D. F.; Gillan, T.; Ingold, K. U. J. Am. Chem. Soc. 1971, 93, 6555.
34. The data for the structure have been deposited with the Cambridge Cystallographic Data Center as supplementary publication no. CCDC-216571.
35. Stegmann, H. B.; Schaber, F.-M.; Schuler, P.; Scheffler, K. Magn. Reson. Chem. 1989, 27, 887.
36. Heller, C.; McConell, H. M. J. Chem. Phys. 1960, 32, 1535.
37. Aurich, H. G. In Nitrones, Nitronates and Nitroxides; Patai, S., Rappoport, Z., Eds. John Wiley & Sons: Chichester, 1989; Chapter 4, p. 338.