Steric and Electronic Effects in Cyclic Alkoxyamines - Synthesis and Applications as Regulators for Controlled/Living Radical Polymerization

Chemistry - A European Journal

Volumn 10, Issue 5, 2004, Pages 1156-1166

  Wetter, Christian ^a   Gierlich, Johannes ^a   Knoop, Christoph Alexander ^a   Müller, Christoph ^a   Schulte, Tobias ^a   Studer, Armido ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Alkoxyamines; Block copolymers; Kinetics; Nitroxides; Radical polymerization

Indexed keywords

BLOCK COPOLYMERS; CHEMICAL BONDS; POLYMERIZATION; PYROLYSIS; REACTION KINETICS; STYRENE; SYNTHESIS (CHEMICAL);

OLEFINATION; POLYDISPERSITIES;

AMINES;

ACRYLIC ACID BUTYL ESTER; AMINE; BISPHOSPHONIC ACID DERIVATIVE; CARBON; COPOLYMER; DIAZOMETHANE; KETONE DERIVATIVE; METHYL GROUP; NITROGEN; OXYGEN; RADICAL; STYRENE; TRIMETHYLSILYL DERIVATIVE; TRIMETHYLSILYL DIAZOMETHANE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CYCLIZATION; DECOMPOSITION; ELECTRIC POTENTIAL; EQUILIBRIUM CONSTANT; HORNER WADSWORTH EMMONS REACTION; KINETICS; MOLECULAR STABILITY; OLEFINATION; POLYMERIZATION; REACTION ANALYSIS; REGULATORY MECHANISM; SILYLATION; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE; THERMOSTABILITY;

EID: 1642358538     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305427     Document Type: Article

References (46)

1. a) D. H. Solomon, E. Rizzardo, P. Cacioli, US Patent 4581429; P. Eur. Pat. Appl. 135280 (Chem. Abstr., 1985, 102, 221335q);
2. a) D. H. Solomon, E. Rizzardo, P. Cacioli, US Patent 4581429; P. Eur. Pat. Appl. 135280 (Chem. Abstr., 1985, 102, 221335q);
3. M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, G. K. Hamer, Macromolecules 1993, 26, 2987;
4. Review: C. J. Hawker, A. W. Bosman, E. Harth, Chem. Rev. 2001, 101, 3661.
5. a) K. Matyjaszewski, J. Xia, Chem. Rev. 2001, 101, 2921;
6. M. Kamigaito, T. Ando, M. Sawamoto, Chem. Rev. 2001, 101, 3689.
7. E. Rizzardo, J. Chiefari, R. T. A. Mayadunne, G. Moad, S. H. Thang, In Controlled/Living Radical Polymerization (Ed.: K. Matyjaszewski), American Chemical Society, Washington DC, 2000, ACS Symposium Series 768, p. 278.
8. H. Fischer, Chem. Rev. 2001, 101, 3581.
9. S. Marque, H. Fischer, E. Baier, A. Studer, J. Org. Chem. 2001, 66, 1146.
10. a) A. Goto, T. Terauchi, T. Fukuda, T. Miyamoto, Macromol. Rapid Commun. 1997, 18, 673;
11. b) T. Fukuda, A. Goto, Macromol. Rapid Commun. 1997, 18, 683;
12. c) W. G. Skene, S. T. Belt, T. J. Connolly, P. Hahn, J. C. Scaiano, Macromolecules 1998, 31, 9103;
13. d) K. Ohno, Y. Tsujii, T. Miyamoto, T. Fukuda, M. Goto, K. Kobayashi, T. Akaike, Macromolecules 1998, 31, 1064;
14. e) S. A. F. Bon, G. Chambard, A. L. German, Macromolecules 1999, 32, 8269;
15. f) A. Goto, T. Fukuda, Macromol. Chem. Phys. 2000, 201, 2138;
16. g) D. Benoit, S. Grimaldi, S. Robin, J.-P. Finet, P. Tordo, Y. Gnanou, J. Am. Chem. Soc. 2000, 122, 5929;
17. h) S. Marque, C. LeMercier, P. Tordo, H. Fischer, Macromolecules 2000, 33, 4403;
18. i) E. Drockenmuller, J.-M. Catala, Macromolecules 2002, 35, 2461;
19. j) D. Bertin, F. Chauvin, S. Marque, P. Tordo, Macromolecules 2002, 35, 3790;
20. k) C. Le Mercier, S. Acerbis, D. Bertin, F. Chauvin, D. Gigmes, O. Guerret, M. Lansalot, S. Marque, F. Le Moigne, H. Fischer, P. Tordo, Macromol. Symp. 2002, 182, 225.
21. T. Schulte, A. Studer, Macromolecules 2003, 36, 3078.
22. G. Moad, E. Rizzardo, Macromolecules 1995, 28, 8722.
23. S. Marque, J. Sobek, H. Fischer, A. Kramer, P. Nesvadba, W. Wunderlich, Macromolecules 2003, 36, 3440. For steric effects in five-membered cyclic nitroxides, see: R. D. Puts, D. Y. Sogah, Macromolecules 1996, 29, 3323.
24. S. Marque, J. Sobek, H. Fischer, A. Kramer, P. Nesvadba, W. Wunderlich, Macromolecules 2003, 36, 3440. For steric effects in five-membered cyclic nitroxides, see: R. D. Puts, D. Y. Sogah, Macromolecules 1996, 29, 3323.
25. G. Büchi, H. Wüest, Helv. Chim. Acta 1979, 62, 2661.
26. M.A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush, T. Sakai, Tetrahedron Lett. 1984, 25, 2183.
27. M. W. Rathke, M. Novak, J. Org. Chem. 1985, 50, 2624.
28. W. R. Couet, R. C. Brasch, G. Sosnovsky, J. Lukszo, I. Prakash, C. T. Gnewuch, T. N. Tozer, Tetrahedron 1985, 41, 1165.
29. K. Matyjaszewski, B. E. Woodworth, X. Zhang, S. G. Gaynor, Z. Metzner, Macromolecules 1998, 31, 5955.
30. M. Ishikawa, H. Sakamoto, T. Tabuchi, Organometallics 1991, 10, 3173.
31. a) A. Naka, T. Okada, M. Ishikawa, J. Organomet. Chem. 1996, 521, 163;
32. b) D. S. Brown, P. T. Gallagher, A. P. Lightfoot, C. J. Moody, A. M. Z. Slawin, E. Swann, Tetrahedron 1995, 51, 11473.
33. a) D. Benoit, V. Chaplinski, R. Braslau, C. J. Hawker, J. Am. Chem. Soc. 1999, 121, 3904;
34. b) D. C. Tully, M. J. Roberts, B. H. Geierstanger, R. B. Grubbs, Macromolecules 2003, 36, 4302.
35. S. Grimaldi, J.-P. Finet, A. Zeghdaoui, P. Tordo, D. Benoit, Y. Gnanou, M. Fontanille, P. Nicol, J.-F. Pierson, PolymerPolym. Prep. 1997, 38, 651.
36. Recently, Hintermann et al. reported the n-butyl acrylate polymerization with a cyclic nitroxide that gave rather good control (PDI = 1.2). However, only low molecular weight polybutyl acrylate was prepared: T. Hintermann, A. Kramer, P. Nesvadba, J. Fink, PolymerPolym. Prep. 2002, 43, 86; C. A. Knoop, A. Studer, J. Am. Chem. Soc. 2003, 125, 16327.
37. Recently, Hintermann et al. reported the n-butyl acrylate polymerization with a cyclic nitroxide that gave rather good control (PDI = 1.2). However, only low molecular weight polybutyl acrylate was prepared: T. Hintermann, A. Kramer, P. Nesvadba, J. Fink, PolymerPolym. Prep. 2002, 43, 86; C. A. Knoop, A. Studer, J. Am. Chem. Soc. 2003, 125, 16327.
38. A. W. Hui, A. E. Hamielec, J. Appl. Polym. Sci. 1972, 16, 749.
39. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, V. G. Z. J. R. Cheeseman, J. A. Montgomery, Jnr., R. E. J. Stratman, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghvachari, J. B. Foresman, J. Cioslowski, J. V. Oritz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzales, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.9 ed., 1998.
40. F. B. van Duijneveldt, J. G. C. M. van Dunijeveldt-van de Rijdt, J. H. van Lenthe, Chem. Rev. 1994, 94, 1873.
41. a) G. A. Kovtun, A. L. Aleksandrov, V. A. Golubev, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1974, 10, 2115;
42. b) J. A. Howard, J. C. Tait, J. Org. Chem. 1978, 43, 4279;
43. D. W. Grattan, D.J. Carlsson, J. A. Howard, D. M. Wiles, Can. J. Chem. 1979, 57, 2834.
44. a) A. Goto, Y. Kwak, C. Yoshikawa, Y. Tsujii, Y. Sugiura, T. Fukuda, Macromolecules 2002, 35, 3520;
45. S. Gennady, G. S. Ananchenko, H. Fischer, J. Polym. Sci. Part A: Polym. Chem. 2001, 39, 3604.
46. Decomposition of 16 was not a clean reaction. In addition to the formation of styrene, other unidentified decomposition products were observed during the NMR studies.