Synlett 2013; 24(10): 1233-1237
DOI: 10.1055/s-0033-1338950
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© Georg Thieme Verlag Stuttgart · New York

N-Heterocyclic Carbene Catalyzed Transesterification of Polytrifluoroethyl Acrylates

Johannes A. M. Hepperle
a  Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstr. 40, 48149 Münster, Germany   Fax: +49(251)8336523   Email: studer@uni-muenster.de
,
Ramesh C. Samanta
b  NRW International Graduate School of Chemistry, Westfälische Wilhelms-Universität, Corrensstr. 40, 48149 Münster, Germany
,
Armido Studer*
a  Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstr. 40, 48149 Münster, Germany   Fax: +49(251)8336523   Email: studer@uni-muenster.de
› Author Affiliations
Further Information

Publication History

Received: 27 March 2013

Accepted after revision: 26 April 2013

Publication Date:
17 May 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.

Supporting Information

 
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