Long-range polar and steric effects in propionate-SG1-type alkoxyamines (SG1-CHMeCOOX): A multiparameter analysis

Journal of Physical Organic Chemistry

Volumn 19, Issue 4, 2006, Pages 269-275

  Ananchenko, Gennady ^a   Beaudoin, Emmanuel ^b   Bertin, Denis ^b   Gigmes, Didier ^b   Lagarde, Pierre ^b   Marque, Sylvain R A ^b   Revalor, Eve ^b   Tordo, Paul ^b  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Alkoxyamines; Homolysis; Long range effects; Multiparameter analysis; Polar and steric effects

Indexed keywords

CHEMICAL ANALYSIS; RATE CONSTANTS;

ALKOXYAMINES; HOMOLYSIS; LONG-RANGE EFFECTS; MULTIPARAMETER ANALYSIS; POLAR AND STERIC EFFECTS; POLARITY; PROPIONATE-SG1-TYPE ALKOXYAMINES; STERIC EFFECTS;

AMINES;

EID: 33745177778     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1035     Document Type: Article

References (54)

1. Solomon DH, Rizzardo E, Cacioli P. US Patent 4,581,429;
2. Eur. Pat. Appl. 135280. Chem. Abstr. 1985; 102: 221335q.
3. Georges MK, Veregin RPN, Kazmaier PM, Hamer GK. Macromolecules 1993; 26: 2987-2988.
4. Hawker CJ. Acc. Chem. Res. 1997; 30: 373-382.
5. Hawker CJ, Bosman AW, Harth E. Chem. Rev. 2001; 101: 3661-3688 and references cited therein.
6. Greszta D, Matyjaszewski K. Macromolecules 1996; 29: 7661-7670 and references cited therein.
7. Fischer H, Souaille M. Chimia 2001; 55: 109-113.
8. Fischer H. Chem. Rev. 2001; 101: 3581-3610 and references cited therein.
9. Goto A, Fukuda T. Prog. Polym. Sci. 2004; 29: 329-385.
10. Matyjaszewski K (ed). Controlled-Living Radical Polymerization: Progress in ATRP, NMP, and RAFT. American Chemical Society: Washington, DC, Vol. 768, 2000;
11. Matyjaszewski K. Macromol. Symp. 2001; 174: 51-68.
12. Moad G, Rizzardo E. Macromolecules 1995; 28: 8722-8728.
13. Grimaldi S, Le Moigne F, Finet J-P, Tordo P, Nicol P, Plechot M. International Patent WO 96/24620. 15 August 1996.
14. Benoit D, Chaplinski V, Braslau R, Hawker CJ. J. Am. Chem. Soc. 1999; 121: 3904-3920.
15. Zink M-O, Kramer A, Nesvadba P. Macromolecules 2000; 33: 8106-8108.
16. 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: 225-247.
17. Couturier J-L, Guerret O, Gigmes D, Marque S, Chauvin F, Dufils P-E, Bertin D, Tordo P. Patent no FR2843394 (2004), WO 2004014926.
18. Marque S, Le Mercier C, Tordo P, Fischer H. Macromolecules 2000; 33: 4403-4410.
19. Marsal P, Roche M, Tordo P, de Sainte Claire P. J. Phys. Chem. A 1999; 103: 29899-29905.
20. Le Mercier C, Lutz J-F, Marque S, Le Moigne F, Tordo P, Lacroix-Desmazes P, Boutevin B, Couturier JL, Guerret O, Martschke R, Sobek J, Fischer H. ACS symp. ser. 2000; 768: 108-122.
21. Bertin D, Gigmes D, Le Mercier C, Marque SRA, Tordo P. J. Org. Chem. 2004; 69: 4925-4930.
22. Bertin D, Gigmes D, Marque SRA, Tordo P. Macromolecules 2005; 38: 2638-2650.
23. Marque S. J. Org. Chem. 2003; 68: 7582-7590.
24. Moad CL, Moad G, Rizzardo E, Thang SH. Macromolecules 1996; 29:7717-7726.
25. Skene WG, Belt ST, Connolly TJ, Hahn P, Scaiano JC. Macromolecules 1998; 31: 9103-9105.
26. Rizzardo E, Chieffari J, Chong BYK, Ercole F, Krstina J, Jeffery J, Le TPT, Mayadunne RTA, Meijs GF, Moad CL, Moad G, Thang SH. Macromol. Symp. 1999; 143: 291-307.
27. Ciriano MV, Korth H-G, van Scheppingen WB, Mulder P. J. Am. Chem. Soc. 1999; 121: 6375-6381.
28. Cameron NR, Reid AJ, Span P, Bon SAF, van Es JJGS, German AL. Macromol. Chem. Phys. 2000; 201: 2510-2518.
29. Goto A, Fukuda T. Macromol. Chem. Phys. 2000; 201: 2138-2142.
30. Marque S, Fischer H, Baier E, Studer A. J. Org. Chem. 2001; 66: 1146-1156.
31. Ananchenko GS, Marque S, Gigmes D, Bertin D, Tordo P. Org. Biomol. Chem. 2004; 2: 709-7014.
32. Ananchenko GS, Matyjaszewski K. Macromolecules 2002; 35: 8323-8329.
33. Bertin D, Gigmes D, Maurin R, Tordo P. J. Polym. Sci.: Part A: Polym. Chem. 2004; 42: 3504-3515.
34. Bertin D, Gigmes D, Marque SRA, Milardo S, Peri J, Tordo P. Coll. Czec. Chem. Commun. 2004; 69: 2223-2238.
35. Kutter E, Hansch C. J. Med. Chem. 1969; 647-652.
36. Fujita T, Takayama C, Nakajima M. J. Org. Chem. 1973; 38:1623-1631.
37. Charton M, Charton BI. J. Chem. Soc., Perkin Trans. 2: 1999; 2203-2211.
38. Bowden K, Grubbs EJ. Progr. Phys. Org. Chem. 1992; 19: 183-224.
39. Bowden K, Grubbs EJ. Chem. Soc. Rev. 1996; 25: 171-182.
40. Juaristi E, Cuevas G. The Anomeric Effect. CRC Press: Boca Raton, FL, 1995.
41. Armarego WLF, Chai CLL. Purification of Laboratory Chemicals (5th edn). Butterworth Heinemann: Amsterdam, 2003.
42. Bertin D, Gigmes D, Marque S, Tordo P. e-Polymers 2003; paper 2.
43. Beaudoin E, Bertin D, Gigmes D, Marque SRA, Siri D, Tordo P. Eur. J. Org. Chem. 2006; 1755-1768.
44. This issue is addressed in a forthcoming review Bertin D, Gigmes D, Marque SRA. Recent Res. Develop. Org. Chem. in press.
45. Héberger K, Kemény S, Vidoczy T. Int. J. Chem. Kin. 1987; 19: 171-181.
46. Charton M. Progr. Phys. Org. Chem. 1981; 13: 119-251.
47. Charton M. In Advances in Quantitatives Structure-Property Relationship. The Estimation of Electrical Effect Substituent Constants for Correlation Analysis. M. Charton (ed.). Jai Press Inc.: Greenwich CT, 1996; 1: 171-219.
48. Charton M. Stud. Org. Chem. 1991; 42: 629-692.
49. Charton M. Top. Curr. Chem. 1983; 114: 57-91.
50. Gallo R. Progr. Phys. Org. Chem. 1983; 14: 115-163.
51. Charton M. Adv. Mol. Struc. Res. 1999; 5: 25-88.
52. Shorter M. In Correlation Analysis of Organic Reactivity. J. Wiley & Sons: New York, 1982, 73-126.
53. Charton M. J. Phys. Org. Chem. 1999; 12: 275-282.
54. Guerret O, Couturier JL, Chauvin F, El-Bouazzy H, Bertin D, Gigmes D, Marque S, Fischer A, Tordo P. ACS symp. ser. 2003; 854: 412-423.