The genesis of the reversible radical addition-fragmentation-transfer of thiocarbonylthio derivatives from the Barton-McCombie deoxygenation: A brief account and some mechanistic observations

Australian Journal of Chemistry

Volumn 59, Issue 10, 2006, Pages 663-668

  Zard, Samir Z ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; POLYMERIZATION; REACTION KINETICS;

RADICAL ADDITION-FRAGMENTATION-TRANSFER; THIOCARBONYLTHIO DERIVATIVES; XANTHATES;

SULFUR COMPOUNDS;

EID: 33750497617     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH06263     Document Type: Article

References (52)

1. (a) D. H. R. Barton, S. W. McCombie, J. Chem. Soc., Parkin Trans. 1 1975, 1574. doi:10.1039/P19750001574
2. (b) D. H. R. Barton, Haifa Century of Free Radical Chemistry 1993 (Cambridge University Press: Cambridge).
3. (a) W. Hartwig, Tetrahedron 1983, 39, 2609. doi: 10.1016/S0040-4020(01) 91972-6
4. (b) D. Crich, L. Quintero, Chem. Rev. 1989, 89, 1413. doi:10.1021/CR00097A001
5. P. J. Barker, A. L. I Beckwith, J. Chem. Soc. Chem. Commun. 1984, 683. doi:10.1039/C39840000683
6. (a) D. H. R. Barton, D. Crich, A. Löbberding, S. Z. Zard, J. Chem. Soc. Chem. Commun. 1985, 646. doi:10.1039/C39850000646
7. (b) D. H. R. Barton, D. Crich, A. Löbberding, S. Z. Zard, Tetrahedron 1986, 42, 2329. doi:10.1016/S0040-4020(01)90614-3 For related mechanistic studies, see:
8. (c) M. D. Bachi, E. Bosch, J. Chem. Soc., Perkin Trans. 1 1988, 1517. doi:10.1039/P19880001517
9. (d) M. D. Bachi, E. Bosch, D. Denenmark, D. Girsh, J. Org. Chem. 1992, 57, 6803. doi:10.1021/JO00051A024
10. B. Quiclet-Sire, S. Z. Zard, Tetrahedron Lett. 1998, 39, 9435. doi: 10.1016/80040-4039(98)02187-X
11. (a) B. Quiclet-Sire, S. Z. Zard, Top. Curr. Chem. 2006, 264, 201.
12. (b) S. Z. Zard, in Radicals in Organic Synthesis (Eds P. Renaud, M. P. Sibi) 2001, Vol. 1, pp. 90-108 (Wiley-VCH: Weinheim).
13. (c) B. Quiclet-Sire, S. Z. Zard, Phosphorus Sulfur Silicon Relat. Elem. 1999, 153-154, 137.
14. (d) B. Quiclet-Sire, S. Z. Zard, J. Chin. Chem. Soc. 1999, 46, 139.
15. (e) S. Z. Zard, Angew. Chem. Int. Ed. 1997, 36, 672. doi: 10.1002/ANIE.199706721
16. (a) H. Henry, DEA Report 1994 (Université Paris XI: Orsay).
17. (b) M. Destarac, X. Franck, D. Charmot, S. Z. Zard, Macromol. Rapid Commun. 2000, 21, 1035. doi: 10.1002/1521-3927 (20001001)21:15〈1035::AID- MARC1035〉3.0.CO;2-5
18. E. Bacqué, F. Pautrat, S. Z. Zard, Chem. Commun. 2002, 2312. doi:10.1039/B206568A
19. M.-P. Denieul, B. Quiclet-Sire, S. Z. Zard, Chem. Commun. 1996, 2511. doi: 10.1039/CC9960002511
20. M. de Greef, Ph.D. Thesis 2006 (Ecole Polytechnique: Palaiseau).
21. F. Gagosz, S. Z. Zard, Org. Lett. 2003, 5, 2655. doi:10.1021/ OL034812M
22. For recent reviews, see: (a) G. Moad, E. Rizzardo, S. H. Thang, Aust. J. Chem. 2005, 58, 379. doi:10.1071/CH05072
23. (b) S. Perrier, T. Takolpuckdee, J. Polym. Sci. Part A Polym. Chem. 2005, 43, 5347. doi:10.1002/POLA.20986
24. P. Corpart, D. Charmot, T. Biadatti, S. Z. Zard, D. Michelet, Int. Pat. WO 9858974 1998 [Chem.Abstr. 1999, 130, 82018].
25. T. P. Le, G. Moad, E. Rizzardo, S. H. Thang, Int. Pat. WO 9801478 1998 [Chem.Abstr. 1998, 128, 115390].
26. (a) M. Destarac, C. Kalai, L. Petit, A. Z. Wilczewska, G. Mignani, S. Z. Zard, Abst, Pap. Am. Chem. Soc. 2005, 230, 533-POLY.
27. (b) S. Z. Zard, B. Sire, P. Jost, Int. Pat. WO 2005040233 2005.
28. H. R. Nace, Org. React. 1962, 12, 57.
29. M. Destarac, C. Kalai, A. Z. Wilczewska, G. Mignani, S. Z. Zard, Abstr. Pap. Am. Chem. Soc. 2005, 250, 535-POLY.
30. M. Bingham, S. Z. Zard, unpublished.
31. (a) J. Xu, J. He, D. Fan, W. Tang, Y. Yang, Macromolecules 2006, 39, 3573. doi:10.1021/MA060184N
32. (b) Y Liu, J. He, J. Xu, D. Fan, W. Tang, Y. Yang, Macromolecules 2005, 38, 10332. doi:10.1021/MA0513970
33. (c) G. Moad, Y K. Chong, A. Postma, E. Rizzardo, S. H. Thang, Polymer 2005, 46, 8458. doi:10.1016/J.POLYMER. 2004.12.061
34. (d) A. Postma, T. P. Davis, G. Moad, M. S. O'Shea, Macromolecules 2005, 38, 5371. doi:10.1021/MA050402X
35. T. Arita, M. Buback, P. Vana, Macromolecules 2005, 38, 7935. doi:10.1021/MA051012D
36. (a) C. Barner-Kowollik, J. F. Quinn, T. L. U. Nguyen, J. P. A. Heuts, T. P. Davis, Macromolecules 2001, 34, 7849. doi:10.1021/MA010349M
37. (b) S. Perrier, C. Barner-Kowollik, J. F. Quinn, P. Vana, T. P. Davis, Macromolecules 2002, 35, 8300. doi:10.1021/MA0203445
38. (c) P. Vana, T. P. Davis, C. Barner-Kowollik, Macromol. Theory Simul. 2002, 11, 823. doi:10.1002/1521-3919(20021101)11:8 〈823::AID- MATS823〉3.0.CO;2-R
39. (d) C. Barner-Kowollik, J. F. Quinn, D. R. Morsley, T. P. Davis, J. Polym. Sci. Part A Polym. Chem. 2001, 39, 1353. doi:10.1002/ POLA.1112
40. (e) C. Barner-Kowollik, T. P. Davis, J. P. A. Heuts, M. H. Stenzel, P. Vana, M. Whittaker, J. Polym. Sci. Part A Polym. Chem. 2003, 41, 365. doi: 10.1002/POLA.10567
41. (f) P. Vana, J. F. Quinn, T. P. Davis, C. Barner-Kowollik, Aust. J. Chem. 2002, 55, 425. doi:10.1071/CH02042
42. (a)Y.Kwak, A. Goto, T. Fukuda, Macromolecules 2004, 57, 1219. doi:10.1021/MA030434P
43. (b)Y. Kwak, A. Gota, Y. Tsujii, Y. Murata, K. Komatsu, T. Fukuda, Macromolecules 2002, 55, 3026. doi:10.1021/MA0118421
44. (c) M. J. Monteiro, H. de Brouwer, Macromolecules 2001, 34, 349. doi:10.1021/MA001484M
45. M. Lampilas, B. Quiclet-Sire, S. Z. Zard, unpublished.
46. M. Alajarin, A. Vidal, M.-M. Ortin, Org. Biomol. Chem. 2003, 1, 4282. doi:10.1039/B310593H
47. (a) M. L. Coote, J. Phys. Chem. A 2005, 109, 1230. doi:10.1021/JP046131U For other theoretical studies of the addition-fragmentation process, see:
48. (b) E. I. Izgorodina, M. L. Coote, J. Phys. Chem. A 2006, 110, 2486. doi:10.1021/JP055158Q
49. (c) M. L. Coote, D. J. Henry, Macromolecules 2005, 38, 1415. doi:10.1021/MA047814A
50. (d) M. L. Coote, L. Radom, Macromolecules 2004, 37, 590. doi:10.1021/MA035477K
51. J. C. Scaia K. U. Ingold, J. Am. Chem. Soc. 1976, 95, 4727. doi:10.1021/JA00432A006
52. A. A. Toy, H. Chaffey-Millar, T. P. Davis, M. H. Stenzel, E. I. Izgorodina, M. L. Coote, C. Barner-Kowollik, Chem. Commun. 2006, 835. doi:10.1039/B515561D