Diastereomeric excess upon cleavage and reformation of diastereomeric alkoxyamines

Organic and Biomolecular Chemistry

Volumn 2, Issue 5, 2004, Pages 709-715

  Ananchenko, Gennady ^a   Marque, Sylvain ^b   Gigmes, Didier ^b   Bertin, Denis ^b   Tordo, Paul ^b  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; ESTERS; FREE RADICALS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RATE CONSTANTS;

DIASTEREOMERIC ALKOXYAMINES; DIASTEREOSELECTIVE HOMOLYSIS;

STEREOCHEMISTRY;

AMINE; FREE RADICAL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; TIME;

AMINES; FREE RADICALS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM; TIME FACTORS;

EID: 1642389247     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b313990e     Document Type: Article

References (54)

1. D. H. Solomon, E. Rizzardo and P. Cacioli, USP 4581429/1983 (Chem. Abstr. 1985, 102, 221335q).
2. M. K. Georges, R. P. N. Veregin, P. M. Kazmaier and G. K. Hamer, Macromolecules, 1993, 26, 2987.
3. C. J. Hawker, A. W. Bosman and E. Harth, Chem. Rev., 2001, 101, 3661 and references therein.
4. A. Studer, Angew. Chem., Int. Ed., 2000, 39, 1108
5. A. Studer, Chem. Eur. J., 2001, 7, 1159
6. C. Leroi, B. Fenet, J.-L. Couturier, O. Guerret and M. A. Ciufolini, Org. Lett., 2003, 5, 1079.
7. H. Fischer, Chem. Rev., 2001, 101, 3581 and references therein.
8. K. Matyjaszewski and J. Xia, Chem. Rev., 2001, 101, 2921.
9. M. Kamigato, T. Ando and M. Sawamoto, Chem. Rev., 2001, 101, 3689.
10. S. Grimaldi, F. Lemoigne, J. P. Finet, P. Tordo and P. Nicol, WO 96/24620
11. D. Benoit, S. Grimaldi, J. P. Finet, P. Tordo, M. Fontanille and Y. Gnanou, ACS Symposium Series, American Chemical Society, 1998, 685, 225
12. D. Benoit, S. Grimaldi, S. Robin, J. P. Finet, P. Tordo and Y. Gnanou, J. Am. Chem. Soc., 2001, 122, 5959
13. C. Farcet, M. Lansalot, B. Charleux, R. Pirri and J. P. Vairon, Macromolecules, 200, 33, 8559
14. J.-F. Lutz, P. Lacroix-Desmazes and B. Boutevin, Macromol. Rapid Commun., 2001, 22, 189
15. P. Lacroix-Desmazes, J.-F. Lutz, F. Chauvin, R. Severac and B. Boutevin, Macromolecules, 2001, 34, 8866.
16. S. Grimaldi, J.-P. Finet, A Zeghdaoui, P. Tordo, D. Benoit, Y. Gnagnou, M. Fontanille, P. Nicol and J.-F. Pierson, Polym. Prepr., 1997, 213, 651.
17. R. Braslau, N. Naik and H. Zipse, J. Am. Chem. Soc., 2000, 122, 8421.
18. M. P. Sibi and N. A. Porter, Acc. Chem. Res., 1999, 32, 163
19. D. P. Curran, N. A. Porter and B. Giese, Stereochemistry of Radical Reactions, VCH, New York, 1996.
20. S. Marque C. Le Mercier, P. Tordo and H. Fischer, Macromolecules, 2000, 33, 4403.
21. K. Matyjaszewski, H.-J. Paik, P. Zhou and S. J. Diamanti, Macromolecules, 2001, 34, 5125.
22. R. D. Puts and D. Y. Sogah, Macromolecules, 1996, 29, 3323.
23. G. S. Ananchenko, M. Souaille, H. Fischer, C. Le Mercier and P. Tordo, J. Polym. Sci., Part A: Polym. Chem., 2002, 40, 3264.
24. G. Ananchenko and K. Matyjaszewski, Macromolecules, 2002, 35, 8323.
25. A more systematic study of the effect of the ester group will be published elsewhere: D. Bertin, D. Gigmes, S. Marque, R. Maurin and P. Tordo, Macromolecules, submitted.
26. T. Fukuda, T. Terauchi, A. Goto, K. Ohno, Y. S. Tsujii, T. Miyamoto, S. Kobatake and B. Yamada, Macromolecules, 1996, 29, 6393.
27. M. Souaille and H. Fischer, Macromolecules, 2001, 34, 2830.
28. G. S. Ananchenko and H. Fischer, J. Polym. Sci., Part A: Polym. Chem., 2001, 39, 3604.
29. T. Kothe, S. Marque, R. Martschke, M. Popov and H. Fischer, J. Chem. Soc., Perkin Trans. 2, 1998, 1553.
30. G. Ananchenko and H. Fischer, J. Chem. Soc., Perkin Trans. 2, 2001, 1887.
31. D. Bertin, D. Gigmes, S. Marque and P. Tordo, E-Polymers, art. no 002, January 16, 2003.
32. K. Matyjaszewski, H.-j. Paik, D. A. Shipp, Y. Isobe and Y. Okamoto, Macromolecules, 2001, 34, 3127.
33. A. K. Nanda and K. Matyjaszewski, Macromolecules, 2003, 36, 1487.
34. J. Sobek, R. Martschke and H. Fischer, J. Am. Chem. Soc., 2001, 123, 2849.
35. M. E. Scott, J. S. Parent, J. Dupont and R. A. Whitney, Ind. Eng. Chem. Res., 2003, 42, 3662
36. C. A. Bacon, N. R. Cameron and A. J. Reid, Macromol. Chem. Phys., 2003, 204, 1923.
37. The influence of the β-alkoxy substituent on H-abstraction rate has been discussed in W. K. Busfield, I. D. Grice and I. D. Jenkins, J. Chem. Soc., Perkin Trans. 2, 1994, 1079
38. I. D. Jenkins, J. Chem. Soc. Chem. Commun., 1994, 1227.
39. A. Goto, Y. Kwak, C. Yoshikawa, Y. Tsujii, Y. Sugiura and T. Fukuda, Macromolecules, 2002, 35, 3530.
40. W. G. Skene, J. C. Sacramento and G. P. A. Yap, Macromolecules, 2000, 33, 3536.
41. A. K. Nanda, G. Anantchenko and K. Matyjaszewski, Polym. Prepr., 2002, 43, 225
42. A. K. Nanda and K. Matyjaszewski, Macromolecules., 2003, 36, 8222.
43. S. Marques, J. Org. Chem., 2003, 68, 7582.
44. D. Bertin, F. Chauvin, S. Marque and P. Tordo, Macromolecules, 2002, 35, 3790
45. O. Guerret, J.-L. Couturier, F. Chauvin, H. El-Bouazzy, D. Bertin, D. Gigmes, S. Marque, H. Fischer and P. Tordo, ACS Symposium Series, American Chemical Society, 2003, 854, 412.
46. A. Goto and T. Fukuda, Macromol. Chem. Phys., 2000, 201, 2138.
47. K. Matyjaszewski, H.-j. Paik, P. Zhou and S. J. Diamanti, Macromolecules, 2001, 34, 5125.
48. H. Fischer, ACS Symposium Series, American Chemical Society, 2003, 854, 10 and references therein.
49. A reference of our earlier work predicted that See refs. 24, 25 in ref. 36.
50. The stereospecific radical polymerization of N-triphenylmethyl methacrylamides has been successfully achieved recently: N. Hoshikawa, Y. Hotta and Y. Okamoto, J. Am. Chem. Soc., 2003, 125, 12380.
51. D. M. Haddleton, D. J. Duncalf, D. Kukuli, A. M. Heming, A. J. Shooter and A. J. Clark, J. Mater. Chem., 1998, 8, 1525.
52. M. Tsuji, R. Sakai, T. Satoh, H. Kaga and T. Kakuchi, Macromolecules, 2002, 35, 8255
53. T. Kakuchi, M. Tsuji and T. Saton, ACS Symposium Series, American Chemical Society, 2003, 854, 206.
54. J.-F. Lutz, D. Neugebauer and K. Matyjaszewski, J. Am. Chem. Soc., 2003, 125, 4735.