RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2013; 24(10): 1233-1237
DOI: 10.1055/s-0033-1338950
DOI: 10.1055/s-0033-1338950
cluster
N-Heterocyclic Carbene Catalyzed Transesterification of Polytrifluoroethyl Acrylates
Weitere Informationen
Publikationsverlauf
Received: 27. März 2013
Accepted after revision: 26. April 2013
Publikationsdatum:
17. Mai 2013 (online)

Abstract
This article describes N-heterocyclic carbene catalyzed transesterification of polytrifluoroethyl acrylates which are readily prepared by nitroxide-mediated radical polymerization using a sterically hindered alkoxyamine as an initiator/regulator. Controlled radical polymerization provides polytrifluoroethyl acrylates with molecular weights (Mn) ranging from 1600 to 17200 g/mol and low molecular weight distributions (polydispersity index, PDI = 1.1–1.2). The polytrifluoroethyl acrylates are readily transesterified with various alcohols in the presence of an NHC catalyst.
Key words
nitroxide-mediated radical polymerization - N-heterocyclic carbenes - esterification - polyacrylates - polymer analogous reactionSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
- 1 Batz H.-G, Franzmann G, Ringsdorf H. Angew. Chem., Int. Ed. Engl. 1972; 11: 1103
- 2 Ferruti P, Bettelli A, Feré A. Polymer 1972; 13: 462
- 3 Günay KA, Theato P, Klok H.-A. J. Polym. Sci., Part A: Polym. Chem. 2013; 51: 1
- 4 Godwin A, Hartenstein M, Müller AH. E, Brocchini S. Angew. Chem. Int. Ed. 2001; 40: 594
- 5 Gibson MI, Fröhlich E, Klok H.-A. J. Polym. Sci., Part A: Polym. Chem. 2009; 47: 4332
- 6 Strong LE, Kiessling LL. J. Am. Chem. Soc. 1999; 121: 6193
- 7 Grasa GA, Kissling RM, Nolan SP. Org. Lett. 2002; 4: 3583
- 8 Movassaghi M, Schmidt MA. Org. Lett. 2005; 7: 2453
- 9 Samanta RC, De Sarkar S, Fröhlich R, Grimme S, Studer A. Chem. Sci. 2013; 4: 2177
- 10 De Sarkar S, Grimme S, Studer A. J. Am. Chem. Soc. 2010; 132: 1190
- 11 Nyce GW, Lamboy JA, Connor EF, Waymouth RM, Hedrick JL. Org. Lett. 2002; 4: 3587
- 12a Fevre M, Pinaud J, Gnanou Y, Vignolle J, Taton D. Chem. Soc. Rev. 2013; 42: 2142
- 12b Zhang Y, Chen EY. X. Angew. Chem. Int. Ed. 2012; 51: 2465
- 13a Hawker CJ, Bosman AW, Harth E. Chem. Rev. 2001; 101: 3661
- 13b Studer A. Chem. Soc. Rev. 2004; 33: 267
- 13c Sciannamea V, Jerome R, Detrembleur C. Chem. Rev. 2008; 108: 1104
- 13d Tebben L, Studer A. Angew. Chem. 2011; 123: 5138
- 14 Miele S, Nesvadba P, Studer A. Macromolecules 2009; 42: 2419
- 15 Fischer H. Chem. Rev. 2001; 101: 3581
- 16a Nielen MW. F. Mass Spectrom. Rev. 1999; 18: 309
- 16b McEwen CN, Peacock PM. Anal. Chem. 2002; 74: 2743
- 16c Wienhöfer IC, Luftmann H, Studer A. Macromolecules 2011; 44: 2510
- 16d Hepperle JA. M, Luftmann H, Studer A. J. Polym. Sci., Part A: Polym. Chem. 2012; 50: 2150
- 16e Montaudo G, Samperi F, Montaudo MS. Prog. Polym. Sci. 2006; 31: 277
- 16f Hart-Smith G, Barner-Kowollik C. Macromol. Chem. Phys. 2010; 211: 1507
- 17 Schulte T, Siegenthaler KO, Luftmann H, Letzel M, Studer A. Macromolecules 2005; 38: 6833