Low-temperature preparations of unimolecular nitroxide initiators for "living" free radical polymerizations

Macromolecules

Volumn 30, Issue 21, 1997, Pages 6445-6450

  Braslau, Rebecca ^a   Burrill II, Leland C ^a   Siano, Michael ^a   Naik, Neeta ^a   Howden, Rodney K ^a   Mahal, Lara K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL POLYMERIZATION; INITIATORS (CHEMICAL); LEAD COMPOUNDS; MONOMERS; NITROGEN OXIDES; OXIDATION; PHOTOLYSIS;

LEAD OXIDE;

POLYOLEFINS;

EID: 0031247664     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma970822p     Document Type: Article

References (48)

1. (a) Moad, G.; Rizzardo, E. Macromolecules 1995, 28, 8722-8728.
2. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K.; Saban, M. Macromolecules 1994, 27, 7228-7229.
3. (c) Hawker, C. J. J. Am. Chem. Soc. 1994, 116, 11185-11186.
4. -1: (a) Arends, I. W. C. E.; Mulder, P.; Clark, K. B.; Wayner, D. D. M. J. Phys. Chem. 1995, 99, 8182-8189. (b) Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 214, 4983-4992.
5. -1: (a) Arends, I. W. C. E.; Mulder, P.; Clark, K. B.; Wayner, D. D. M. J. Phys. Chem. 1995, 99, 8182-8189. (b) Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 214, 4983-4992.
6. A caveat to this assumption has recently been published: Connolly, T. J.; Scaiano, J. C. Tetrahedron Lett. 1997, 38, 1133-1136.
7. Hawker, C. J.; Barclay, G. G.; Orellana, A.; Dao, J.; Devonport, W. Macromolecules 1996, 29, 5245-5254.
8. Howell, B. A.; Priddy, D. B.; Li, I. Q.; Smith, P. B.; Kastl, P. E. Polym. Bull. 1996, 37, 451-456.
9. Braslau, R.; Burrill, L. C.; Mahal, L. K.; Wedeking, T. Ang. Chem. Int. Ed. Engl. 1997, 36, 237-238.
10. (a) See ref 4 and references contained therein.
11. (b) Connolly, T. J.; Baldovi, M. V.; Mohtat, N.; Scaiano, J. C. Tetrahedron Lett. 1996, 37, 4919-4922.
12. (c) Korolenko, E. C.; Cozens, F. L.; Scaiano, J. C. J. Phys. Chem. 1995, 99, 14123-14128.
13. (d) Catala, J. M.; Bubel, F.; Hammouch, S. O. Macromolecules 1995, 28, 8441-8443.
14. Schmidt, S. P.; Brooks, D. W. Tetrahedron Lett. 1987, 28, 767-768.
15. Michon, P.; Rassat, A. Bull. Soc. Chim. Fr. 1971, 3561-3567.
16. a. Busfield, W. K.; Jenkins, I. D.; Thang, S. H.; Moad, G.; Rizzardo, E.; Solomon, D. H. J. Chem. Soc., Chem. Commun. 1985, 1249-1250.
17. (b) Brown, T. M.; Cooksey, C. H.; Crich, D.; Dronsfield, A. T.; Ellis, R. J. Chem. Soc., Perkin Trans. 1993, 2131-2136.
18. (c) Busfield, K. W.; Engelhardt, L. M.; Healy, P. C.; Jenkins, I. D.; Thang, S. H.; White, A. H. Aust. J. Chem. 1986, 39, 357-365.
19. Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457-4460.
20. -1-Dicarbonyl-Eisen-Komplexen. Ph.D. Dissertation, Universität Basel, 1990; p 109.
21. (b) Peyman, A.; Beckhaus, H.-D.; Kramer, D.; Peters, K.; von Schnering, H. G.; Rüchardt, C. Chem. Ber. 1991, 124, 1989-1996.
22. Mendenhall, G. D.; Protasiewicz, J. D.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1994, 116, 1718-1724.
23. Corey, E. J.; Gross, A. W. J. Org. Chem. 1985, 50, 5391-5393.
24. The addition of alkylhydrazine to the lead/nitroxide suspension can be carried out at room temperature or at -78 °C.
25. See ref 6 for more examples.
26. (a) Falck, J. R.; Mekonnen, B.; Yu, J. R.; Lai, J. Y. J. Am. Chem. Soc. 1996, 118, 6096-6097.
27. (b) You, S.; Neuenschwander, M. Chimia 1992, 46, 377-380.
28. (a) Ramig, K.; Kuzemko, M. A.; McNamara, K.; Cohen, T. J. Org. Chem. 1992, 57, 1968-1969.
29. (b) Schwartz, E. B.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1992, 114, 10775-10784.
30. (c) Poupart, M.-A. Lassalle, G.; Paquette, L. A. Org. Synth. 1990, 69, 173-179.
31. (a) See ref 11.
32. (b) Porter, N. A.; Rosenstein, I. J. Tetrahedron Lett. 1993, 34, 7865-7868.
33. (c) Langer, T.; Illich, M.; Helmchen, G. Tetrahedron Lett. 1995, 36, 4409-4412.
34. Johnston, L. J.; Tencer, M.; Scaiano, J. C. J. Org. Chem. 1986, 51, 2806-2808.
35. For a photolytic method effective with primary alkyl halide substrates based on cobalt, see: Brown, T. M.; Cooksey, C. J.; Crich, D.; Dronsfield, A. T.; Ellis, R. J. Chem. Soc., Perkin Trans. 1 1993, 2131-2136.
36. Giese, B.; Thoma, G. Helv. Chim. Acta 1991, 74, 1135-1142.
37. (a) Busfield, W. K.; Heiland, K.; Jenkins, I. D. Tetrahedron Lett. 1995, 36, 1109-1112.
38. (b) Busfield, W. K.; Heiland, K.; Jenkins, I. D. Tetrahedron Lett. 1994, 35, 6541-6542.
39. Carloni, P.; Damiani, E.; Iacussi, M.; Greci, L.; Stipa, P.; Cauzi, D.; Rizzoli, C.; Sgarabotto, P. Tetrahedron 1995, 57, 12445-12452.
40. (a) See ref 4.
41. (b) Rizzardo, E.; Serelis, A. K.; Solomon, D. H. Aust. J. Chem. 1982, 35, 2013-2024.
42. (a) See ref 2a.
43. (b) Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1988, 53, 1629-1632.
44. Busfield, W. K.; Grice, D. I.; Jenkins, I. D.; Thang, S. H. Aust. J. Chem. 1991, 44, 1407-1415.
45. (a) Mendenhall, G. D. Tetrahedron Lett. 1983, 24, 451-452.
46. (b) Ogle, C. A. Martin, S. W.; Dziobak, M. P.; Urban, M. W.; Mendenhall, G. D. J. Org. Chem. 1983, 48, 3728-3733.
47. (c) The immediate precursor, sodium hyponitrite was purchased from the Michigan Technological University by contacting Prof. Mendenhall.
48. Mendenhall, G. D.; Protasiewicz, J. D.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1994, 116, 1718-1724.