1-tert-Butyl-3,3,5,5-tetraalkyl-2-piperazinon-4-oxyls: Highly Efficient Nitroxides for Controlled Radical Polymerization

Macromolecules

Volumn 42, Issue 7, 2009, Pages 2419-2427

  Miele, Saskia ^a   Nesvadba, Peter ^b   Studer, Armido ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b CIBA GEIGY LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXYAMINE INITIATORS; ALKOXYAMINES; ALKYL GROUPS; CONTROLLED RADICAL POLYMERIZATION; HOMOLYSIS; N-BUTYL ACRYLATE; NITROXIDE MEDIATED RADICAL POLYMERIZATION; NITROXIDES;

ALKYLATION; AMINES; ATOM TRANSFER RADICAL POLYMERIZATION; NITROGEN OXIDES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; POLYMERS; STYRENE;

RATE CONSTANTS;

EID: 66149168595     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma802600x     Document Type: Article

References (81)

1. (a) Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921-2990.
2. (b) Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101, 3689-3746.
3. (c) Tsarevsky, N. V.; Matyjaszewski, K. Chem. Rev. 2007,107, 2270-2299.
4. (d) Ouchi, M.; Terashima, T.; Sawamoto, M. Acc. Chem. Res. 2008, 41, 1120-1132.
5. (a) Barner-Kowollik, C.; Davis, T. P.; Heuts, J. P. A.; Stenzel, M. H.; Vana, P.; Whittaker, M. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 365-375.
6. (b) Rizzardo, E.; Chiefari, J.; Mayadunne, R. T. A.; Moad, G.; Thang, S. H. In Controlled/Living Radical Polymerization; Matyjaszewski, K., Ed.; ACS Symposium Series 768; American Chemical Society: Washington, DC, 2000; p 278.
7. (c) Favier, A.; Charreyre, M.-T. Macromol. Rapid Commun. 2006, 27, 653-692.
8. (d) Barner-Kowollik, C.; Perrier, S. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 5715-5723.
9. (e) Moad, G.; Rizzardo, E.; Thang, S. H. Acc. Chem. Res. 2008, 41, 1133-1142.
10. David, G.; Boyer, C.; Tonnar, J.; Ameduri, B.; Lacroix-Desmazes, P.; Boutevin, B. Chem. Rev. 2006, 106, 936-3962.
11. (a) Yamago, S. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1-12.
12. (b) Yamago, S.; Kayahara, E.; Kotani, M.; Ray, B.; Kwak, Y.; Goto, A.; Fukuda, T. Angew. Chem., Int. Ed. 2007, 46, 1304-1306.
13. (c) Kwak, Y.; Tezuka, M.; Goto, A.; Fukuda, T.; Yamago, S. Macromolecules 2007, 40, 1881-1885.
14. (a) Wayland, B. B.; Poszmik, G.; Mukerjee, S. L.; Fryd, M. J. Am. Chem. Soc. 1994, 116, 7943-7944.
15. (b) Kaneyoshi, H.; Matyjaszewski, K. Macromolecules 2006, 39, 2757-2763, and references cited therein.
16. (c) Poli, R. Angew. Chem., Int. Ed. 2006, 45, 5058-5070.
17. (a) Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661-3688.
18. (b) Sciannamea, V.; Jerome, R.; Detrembleur, C. Chem. Rev. 2008, 108, 1104-1126.
19. Fischer, H. Chem. Rev. 2001, 101, 3581-3610.
20. (a) Studer, A. Chem.-Eur. J. 2001, 7, 1159-1164.
21. (b) Studer, A. Chem. Soc. Rev. 2004, 33, 267-273.
22. (c) Studer, A.; Schulte, T. Chem. Rec. 2005, 5, 27-35.
23. For a discussion on advantages or disadvantages of ATRP, RAFT, and NMP, see: Ansong, O.; Jansen, S.; Wie, Y.; Pomrink, G.; Lu, H.; Patel, A.; Li, S. Polym. Int. 2009, 58, 54-65.
24. Marque, S.; Fischer, H.; Baier, E.; Studer, A. J. Org. Chem. 2001, 66, 1146-1156.
25. (a) Matyjaszewski, K.; Gaynor, S.; Greszta, D.; Mardare, D.; Shigemoto, T. J. Phys. Org. Chem. 1995, 8, 306-315.
26. (b) Matyjaszewski, K.; Gaynor, S.; Greszta, D.; Mardare, D.; Shigemoto, T. Macromol. Symp. 1995, 98, 73-89.
27. (c) Goto, A.; Kwak, Y.; Yoshikawa, C.; Tsujii, Y.; Sugiura, Y.; Fukuda, T. Macromolecules 2002, 35, 3520-3525.
28. Harth, E.; Van Horn, B.; Hawker, C. J. Chem. Commun. 2001, 823-824.
29. Knoop, C. A.; Studer, A. J. Am. Chem. Soc. 2003, 125, 16327-16333.
30. Braslau, R.; O'Bryan, G.; Nilsen, A.; Henise, J.; Thongpaisanwong, T.; Murphy, E.; Mueller, L.; Ruehl, J. Synthesis 2005, 9, 1496-1506.
31. Yin, M.; Krause, T.; Messerschmidt, M.; Habicher, W. D.; Voit, B. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 1873-1882.
32. (a) Bertin, D.; Gigmes, D.; Le Mercier, C.; Marque, S. R. A.; Tordo, P. J. Org. Chem. 2004, 69, 4925-4930.
33. (b) Bertin, D.; Gigmes, D.; Marque, S. R. A.; Milardo, S.; Peri, J.; Tordo, P. Collect. Czech. Chem. Commun. 2004, 69, 2223-2238.
34. (c) Bertin, D.; Gigmes, D.; Marque, S. R. A.; Tordo, P. Macromolecules 2005, 38, 2638-2650.
35. Wetter, C.; Gierlich, J.; Knoop, C.; Muller, C.; Schulte, T.; Studer, A. ChemsEur. J. 2004, 10, 1156-1166.
36. (a) Marque, S.; Sobek, J.; Fischer, H.; Kramer, A.; Nesvadba, P.; Wunderlich, W. Macromolecules 2003, 36, 3440-3442.
37. (b) Nesvadba, P.; Bugnon, L.; Sift, R. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 3332-3341.
38. (c) Studer, A.; Harms, K.; Knoop, C.; Muller, C.; Schulte, T. Macromolecules 2004, 37, 27-34.
39. Siegenthaler, K. O.; Studer, A. Macromolecules 2006, 39, 1347-1352.
40. Chang, C.-C.; Studer, A. Macromolecules 2006, 39, 4062-4068.
41. Chang, C.-C.; Siegenthaler, K. O.; Studer, A. Helv. Chim. Acta 2006, 2200-2210.
42. Molawi, K.; Studer, A. Chem. Commun. 2007, 48, 5173-5175.
43. (a) Goto, A.; Terauchi, T.; Fukuda, T.; Miyamoto, T. Macromol. Rapid Commun. 1997, 18, 673-681.
44. (b) Fukuda, T.; Goto, A. Macromol. Rapid Commun. 1997, 18, 683-688.
45. (c) Skene, W. G.; Belt, S. T.; Conolly, T. J.; Hahn, P.; Scaiano, J. C. Macromolecules 1998, 31, 9103-9105.
46. (d) Ohno, K.; Tsujii, Y.; Miyamoto, T.; Fukuda, T.; Goto, M.; Kobayashi, K.; Akaike, T. Macromolecules 1998, 31, 1064-1069.
47. (e) Bon, S. A. F.; Chambard, G.; German, A. L. Macromolecules 1999, 32, 8269-8276.
48. (f) Goto, A.; Fukuda, T. Macromol. Chem. Phys. 2000, 201, 2138-2142.
49. (g) Fischer, H.; Souaille, M. Chimia 2001, 55, 109-113.
50. (h) Marque, S.; LeMercier, C.; Tordo, P.; Fischer, H. Macromolecules 2000, 33, 4403-4410.
51. (i) Drockenmuller, E.; Catala, J.-M. Macromolecules 2002, 35, 2461-2466.
52. (j) Bertin, D.; Chauvin, F.; Marque, S.; Tordo, P. Macromolecules 2002, 35, 3790-3791.
53. (k) LeMercier, 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, 225-247.
54. (l) Cunningham, M. F.; Tortosa, K.; Lin, M.; Keoshkerian, B.; Georges, M. K. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2828-2841.
55. (m) Cresidio, S. P.; Aldabbagh, F.; Busfield, W. K.; Jenkins, I. D.; Thang, S. H.; Zayas- Holdsworth, C.; Zetterlund, P. B. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 1232-1241.
56. (n) Blomberg, S.; Ostberg, S.; Harth, E.; Bosman, A. W.; Van Horn, B.; Hawker, C. J. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 1309-1320.
57. (o) Dervan, P.; Aldabbagh, F.; Zetterlund, P. B.; Yamada, B. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 327-334.
58. (p) Braslau, R.; O'Bryan, G.; Nilsen, A.; Henise, J.; Thongpaisanwong, T.; Murphy, E.; Mueller, L.; Ruehl, J. Synthesis 2005, 1496-1506.
59. (q) Lagrille, O.; Cameron, N. R.; Lovell, P. A.; Blanchard, R.; Goeta, A. E.; Koch, R. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1926-1940.
60. (r) O'Bryan, G.; Nilsen, A.; Braslau, R. Macromolecules 2007, 40, 7848-7854.
61. (s) Debuigne, A.; Chan-Seng, D.; Li, L.; Hamer, G. K.; Georges, M. K. Macromolecules 2007, 40, 6224-6232.
62. (t) Mannan, M. A.; Ichikawa, A.; Miura, Y. Polymer 2007, 48743-749.
63. Efficient noncyclic systems: Benoit, D.; Chlapinski, V.; Braslau, R.; Hawker, C. J. J. Am. Chem. Soc. 1999, 121, 3904-3920, and ref 16.
64. (a) Marque, S.; Sobek, J.; Fischer, H.; Kramer, A.; Nesvadba, P.; Wunderlich, W. Macromolecules 2003, 36, 3440-3442.
65. (b) Nesvadba, P.; Kramer, A.; Zink, M.-O. Heterocyclic Alkoxyamines as Regulators in Controlled Radical Poloymerization Processes. US Patent 6,479,608, Nov 12, 2002.
66. Kehr, S.; Luftmann, H. e-Polym. 2007, 010.
67. (a) Lai, J. T. J. Org. Chem. 1980, 45, 754-755.
68. (b) Lai, J. T. Synthesis 1981, 40-42.
69. (c) Lai, J. T. Synthesis 1984, 122-123.
70. (d) Lai, J. T. Synthesis 1984, 124-125.
71. Matyjaszewski, K.; Woodworth, B. E.; Zhang, X.; Gaynor, S. G.; Metzner, Z. Macromolecules 1998, 31, 5955-5957.
72. Schulte, T.; Siegenthaler, K. O.; Luftmann, H.; Letzel, M.; Studer, A. Macromolecules 2005, 38, 6833-6840.
73. Edeleva, M.; Marque, S. R. A.; Bertin, D.; Gigmes, D.; Guillaneuf, Y.; Morozov, S. V.; Bagryanskaya, E. G. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 6828-6842.
74. Marque, S.; Le Mercier, C.; Tordo, P.; Fischer, H. Macromolecules 2000, 33, 4403-4410.
75. Schulte, T.; Knoop, C. A.; Studer, A. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 3342-3351.
76. Lacroix-Demazes, P.; Lutz, J.-F.; Boutevin, B. Macromol. Chem. Phys. 2000, 201, 662-669.
77. Fukuda, T.; Goto, A.; Ohno, K. Macromol. Rapid Commun. 2000, 21, 151-165.
78. Souaille, M.; Fischer, H. Macromolecules 2002, 35, 248-261.
79. (a) Marque, S. R. A. J. Org. Chem. 2003, 68, 7582-7590.
80. (b) Fischer, H.; Marque, S. R. A.; Nesvadba, P. Helv. Chim. Acta 2006, 89, 2330-2340.
81. Lacroix-Demazes, P.; Lutz, J.-F.; Chauvin, F.; Severac, R.; Boutevin, B. Macromolecules 2001, 34, 8866-8871.