Collect. Czech. Chem. Commun. 2004, 69, 2223-2238
https://doi.org/10.1135/cccc20042223

Long-Range Polar Effect on the C-ON Bond Homolysis in (tert-Butyl[1-(diethylphosphonyl)-2,2-dimethylpropyl]aminoxyl) SG1-Based Alkoxyamines

Denis Bertin, Didier Gigmes, Sylvain R. A. Marque*, Stephan Milardo, Jérôme Peri and Paul Tordo

Université de Provence, UMR 6517 case 542, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France

References

1. U.S. 4,581,429; Eur. Pat. Appl. 135280; Solomon D. H., Rizzardo E., Cacioli P.: Chem. Abstr. 1985, 102, 221335.
2. Georges M. K., Veregin R. P. N., Kazmaier P. M., Hamer G. K.: Macromolecules 1993, 26, 2987. <https://doi.org/10.1021/ma00063a054>
3a. Hawker C. J.: Acc. Chem. Res. 1997, 30, 373. <https://doi.org/10.1021/ar960248m>
3b. Hawker C. J., Bosman A. W., Harth E.: Chem. Rev. 2001, 101, 3661; and references therein. <https://doi.org/10.1021/cr990119u>
4. Greszta D., Matyjaszewski K.: Macromolecules 1996, 29, 7661. <https://doi.org/10.1021/ma9608840>
5a. Fischer H.: J. Am. Chem. Soc. 1986, 108, 3925. <https://doi.org/10.1021/ja00274a012>
5b. Daikh B. E., Finke R. G.: J. Am. Chem. Soc. 1992, 114, 2938. <https://doi.org/10.1021/ja00034a028>
5c. Fischer H.: Chem. Rev. 2001, 101, 3581; and references therein. <https://doi.org/10.1021/cr990124y>
6a. Fischer H.: Macromolecules 1997, 303, 5666. <https://doi.org/10.1021/ma970535l>
6b. Fischer H.: J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 1885. <https://doi.org/10.1002/(SICI)1099-0518(19990701)37:13<1885::AID-POLA1>3.0.CO;2-1>
6c. Fischer H., Souaille M.: Chimia 2001, 55, 109.
7a. Souaille M., Fischer H.: Macromolecules 2000, 33, 7378. <https://doi.org/10.1021/ma000689s>
7b. Souaille M., Fischer H.: Macromolecules 2001, 34, 2830. <https://doi.org/10.1021/ma001886u>
7c. Souaille M., Fischer H.: Macromolecules 2002, 35, 248. <https://doi.org/10.1021/ma010880h>
7d. Souaille M., Fischer H.: Macromol. Symp. 2001, 174, 231.
8a. Skene W. G., Belt S. T., Connolly T. J., Hahn P., Scaiano J. C.: Macromolecules 1998, 31, 9103. <https://doi.org/10.1021/ma9812229>
8b. Fukuda T., Goto A., Ohno K.: Macromol. Rapid Commun. 2000, 21, 151. <https://doi.org/10.1002/(SICI)1521-3927(200003)21:4<151::AID-MARC151>3.0.CO;2-3>
8c. Le Mercier C., Lutz J.-F., Marque S., Le Moigne F., Tordo P., Lacroix-Desmazes P., Boutevin B., Couturier J.-L., Guerret O., Martschke R., Sobek J., Fischer H.: ACS Symp. Ser. 2000, 768, 108. <https://doi.org/10.1021/bk-2000-0768.ch008>
8d. Cameron N. R., Reid A. J., Span P., Bon S. A. F., van Es J. J. G. S., German A. L.: Macromol. Chem. Phys. 2000, 201, 2510. <https://doi.org/10.1002/1521-3935(20001101)201:17<2510::AID-MACP2510>3.0.CO;2-S>
8e. Goto A., Fukuda T.: Macromol. Chem. Phys. 2000, 201, 2138. <https://doi.org/10.1002/1521-3935(20001101)201:16<2138::AID-MACP2138>3.0.CO;2-1>
8f. Marque S., Fischer H., Baier E., Studer A.: J. Org. Chem. 2001, 66, 1146. <https://doi.org/10.1021/jo001190z>
8g. 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. <https://doi.org/10.1002/1521-3900(200206)182:1<225::AID-MASY225>3.0.CO;2-X>
8h. Bertin D., Chauvin F., Marque S., Tordo P.: Macromolecules 2002, 35, 3790. <https://doi.org/10.1021/ma011945j>
8i. Guerret O., Couturier J.-L., Chauvin F., El-Bouazzy H., Bertin D., Gigmes D., Marque S., Fischer A., Tordo P.: ACS Symp. Ser. 2003, 854, 412. <https://doi.org/10.1021/bk-2003-0854.ch029>
8j. Marque S., Sobek J., Fischer H., Kramer A., Nesvadba P., Wunderlich W.: Macromolecules 2003, 36, 3440. <https://doi.org/10.1021/ma021605d>
8k. Schulte T., Studer A.: Macromolecules 2003, 36, 3078. <https://doi.org/10.1021/ma025806t>
8l. Miura Y., Nakamura N., Taniguchi I., Ichikawa A.: Polymer 2003, 44, 3461. <https://doi.org/10.1016/S0032-3861(03)00275-1>
8m. Cameron N. R., Bacon C. A., Reid A. J.: ACS Symp. Ser. 2003, 854, 452. <https://doi.org/10.1021/bk-2003-0854.ch032>
8n. Knoop C., Studer A.: J. Am. Chem. Soc. 2003, 125, 16327. <https://doi.org/10.1021/ja037948o>
8o. Studer A., Harms K., Knoop C., Müller C., Schulte T.: Macromolecules 2004, 37, 27. <https://doi.org/10.1021/ma035128q>
8p. Wetter C., Gierlich J., Knoop C. A., Müller C., Schulte T., Studer A.: Chem. Eur. J. 2004, 10, 1156. <https://doi.org/10.1002/chem.200305427>
8q. Drockenmuller E., Lamps J.-P., Catala J.-M.: Macromolecules 2004, 37, 2076. <https://doi.org/10.1021/ma0351221>
8r. For kc values: Chateauneuf J., Lusztyk J., Ingold K. U.: J. Org. Chem. 1988, 53, 1629. <https://doi.org/10.1021/jo00243a007>
8s. Chateauneuf J., Lusztyk J., Ingold K. U.: J. Org. Chem. 1990, 55, 1061. <https://doi.org/10.1021/jo00290a046>
8t. Beckwith A. L. J., Bowry V. W., Ingold K. U.: J. Am. Chem. Soc. 1992, 114, 4983. <https://doi.org/10.1021/ja00039a005>
8u. Bowry V. W., Ingold K. U.: J. Am. Chem. Soc. 1992, 114, 4992. <https://doi.org/10.1021/ja00039a006>
8v. Skene W. G., Scaiano J. C., Listigover N. A., Kazmaier P. M., Georges M. K.: Macromolecules 2000, 33, 5065. <https://doi.org/10.1021/ma991753c>
8w. Sobek J., Martschke R., Fischer H.: J. Am. Chem. Soc. 2001, 123, 2849. <https://doi.org/10.1021/ja0036460>
8x. Lebedeva N. V., Zubenko D. P., Bagryanskaya E. G., Sagdeev R. Z., Ananchenko G. S., Marque S., Bertin D., Tordo P.: Phys. Chem. Chem. Phys. 2004, 6, 2254. <https://doi.org/10.1039/b401093k>
9a. Marque S., Le Mercier C., Tordo P., Fischer H.: Macromolecules 2000, 33, 4403. <https://doi.org/10.1021/ma9918452>
9b. Marsal P., Roche M., Tordo P., de Sainte Claire P.: J. Phys. Chem. A 1999, 103, 2899. <https://doi.org/10.1021/jp990202l>
10a. Moad G., Rizzardo E.: Macromolecules 1995, 28, 8722. <https://doi.org/10.1021/ma00130a003>
10b. Moad C. L., Moad G., Rizzardo E., Thang S. H.: Macromolecules 1996, 29, 7717. <https://doi.org/10.1021/ma960852c>
10c. Rizzardo E., Chieffari J., Chong B. Y. K., Ercole F., Krstina J., Jeffery J., Le T. P. T., Mayadunne R. T. A., Meijs G. F., Moad C. L., Moad G., Thang S. H.: Macromol. Symp. 1999, 143, 291. <https://doi.org/10.1002/masy.19991430122>
10d. Ciriano M. V., Korth H.-G., van Scheppingen W. B., Mulder P.: J. Am. Chem. Soc. 1999, 121, 6375. <https://doi.org/10.1021/ja9837102>
11. Marque S.: J. Org. Chem. 2003, 68, 7582. <https://doi.org/10.1021/jo030036k>
12. TEMPO is the 2,2,6,6-tetramethylpiperidine-N-oxyl and DBNO is the di-tert-butyl-N-oxyl, both nitroxyl radicals are commercially available and their corresponding alkoxyamines are of easy access.
13a. Matyjaszewski K.: Controlled Radical Polymerization, Vol. 685. American Chemical Society, Washington (D.C.) 1998.
13b. Matyjaszewski K.: Controlled-Living Radical Polymerization: Progress in ATRP, NMP, and RAFT, Vol. 768. American Chemical Society, Washington (D.C.) 2000.
13c. Matyjaszewski K.: Macromol. Symp. 2001, 174, 51. <https://doi.org/10.1002/1521-3900(200109)174:1<51::AID-MASY51>3.0.CO;2-2>
13d. Matyjaszewski K.: Advances in Controlled/Living Radical Polymerization, Vol. 854. American Chemical Society, Washington (D.C.) 2003.
14a. Grimaldi S., Le Moigne F., Finet J.-P., Tordo P., Nicol P., Plechot M.: Int. WO 96/24620, August 15, 1996; Chem. Abstr. 1996, 125, 223522.
14b. Grimaldi S., Finet J.-P., Zeghdaoui A., Tordo P., Benoit D., Gnagnou Y., Fontanille M., Nicol P., Pierson J.-F.: Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1997, 213, 651.
14c. Grimaldi S., Finet J.-P., Le Moigne F., Zeghdaoui A., Tordo P., Benoit D., Fontanille M., Gnanou Y.: Macromolecules 2000, 33, 1141. <https://doi.org/10.1021/ma9913414>
14d. Gigmes D., Marque S., Guerret O., Couturier J.-L., Chauvin F., Dufils P.-E., Bertin D., Tordo P.: Fr. 2843394, 2004; WO 2004014926; Chem. Abstr. 2004, 140, 164357.
15. Bertin D., Gigmes D., Marque S., Maurin R., Tordo P.: J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 3504. <https://doi.org/10.1002/pola.20178>
16. Ananchenko G., Marque S., Gigmes D., Bertin D., Tordo P.: Org. Biomol. Chem. 2004, 2, 709. <https://doi.org/10.1039/b313990e>
17. Armarego W. L. F., Chai C. L. L.: Purification of Laboratory Chemicals, 5th ed. Butterworth Heinemann, Amsterdam 2003.
18. Le Mercier C.: Ph.D. Thesis. University of Provence, Marseille 2000.
19. Bertin D., Gigmes D., Marque S., Tordo P.: e-Polymers 2003, paper 2.
20a. Charton M.: Prog. Phys. Org. Chem. 1981, 13, 119. <https://doi.org/10.1002/9780470171929.ch3>
20b. Charton M.: Prog. Phys. Org. Chem. 1987, 16, 287. <https://doi.org/10.1002/9780470171950.ch6>
21a. Exner O.: J. Phys. Org. Chem. 1999, 12, 265. <https://doi.org/10.1002/(SICI)1099-1395(199904)12:4<265::AID-POC124>3.0.CO;2-O>
21b. Charton M.: J. Phys. Org. Chem. 1999, 12, 275. <https://doi.org/10.1002/(SICI)1099-1395(199904)12:4<275::AID-POC125>3.0.CO;2-K>
21c. Exner O., Charton M., Galkin V.: J. Phys. Org. Chem. 1999, 12, 289. <https://doi.org/10.1002/(SICI)1099-1395(199904)12:4<289::AID-POC127>3.0.CO;2-1>
22. Charton M.: Adv. Mol. Struc. Res. 1999, 5, 25. <https://doi.org/10.1016/S1087-3295(99)80004-8>
23. DFT calculations were performed at the UB3LYP/6-31G(d) level. Calculated hydrogen hyperfine coupling constants a = 2.07 mT and a = 2.30 mT are in the range for that type of alkyl radical24, unpaired electron densities are 0.875, –0.069, 0.180, –0.001 and –0.01 for C8, C10, O (C=O), O and C11, respectively.
24. Knuehl B., Marque S., Fischer H.: Helv. Chim. Acta 2001, 84, 2290. <https://doi.org/10.1002/1522-2675(20010815)84:8<2290::AID-HLCA2290>3.0.CO;2-O>
25a. Nau W. M.: J. Org. Chem. 1996, 61, 8312. <https://doi.org/10.1021/jo961301n>
25b. Nau W. M.: J. Phys. Org. Chem. 1997, 10, 445. Nau used the term Polar Ground State Effect (PGSE), but the term Polar Molecular State Effect (PMSE) is preferred because ground state is generally used in conjunction with photo-reactions, as pointed out by a referee. <https://doi.org/10.1002/(SICI)1099-1395(199706)10:6<445::AID-POC904>3.0.CO;2-Z>
26. Reichardt C.: Solvents and Solvent Effects in Organic Chemistry, 3rd ed., p. 147. Wiley-VCH, Weinheim 2003.