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Synthesis of alkoxyamine initiators for controlled radical polymerization

Tirrell, David A. (1998) Synthesis of alkoxyamine initiators for controlled radical polymerization. Journal of Polymer Science Part A: Polymer Chemistry, 36 (14). pp. 2667-2668. ISSN 0887-624X. https://resolver.caltech.edu/CaltechAUTHORS:TIRjpsa1998

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Abstract

On page 2161 of this volume, Hawker and coworkers report a simple and efficient method for the synthesis of alkoxyamine initiators for controlled radical polymerization. The method involves treatment of a styrene derivative with (salen)manganese(III) chloride and an oxidant, trapping of the intermediate adduct with 2,2,6,6-tetramethylpiperidinyloxy (TEMPO), and reduction with sodium borohydride. The method works nicely as a one-pot procedure and provides the target alkoxyamines in yields of ca. 55–75%. An attractive feature of the synthesis is the fact that hydroxyl, ester, halide, and alkene functional groups can be tolerated without loss of yield, suggesting that appropriately-substituted alkoxyamine initiators should become readily available for the preparation of polymers of controlled endgroup functionality.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/(SICI)1099-0518(199810)36:14<2667::AID-POLA26>3.0.CO;2-FDOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/(SICI)1099-0518(199810)36:14%3C2667::AID-POLA26%3E3.0.CO;2-F/abstractPublisherArticle
ORCID:
AuthorORCID
Tirrell, David A.0000-0003-3175-4596
Additional Information:Copyright © 1998 John Wiley & Sons, Inc.
Issue or Number:14
Record Number:CaltechAUTHORS:TIRjpsa1998
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:TIRjpsa1998
Official Citation:Tirrell, D. A. (1998), Synthesis of alkoxyamine initiators for controlled radical polymerization. J. Polym. Sci. A Polym. Chem., 36: 2667–2668. doi: 10.1002/(SICI)1099-0518(199810)36:14<2667::AID-POLA26>3.0.CO;2-F
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:53433
Collection:CaltechAUTHORS
Deposited By: Anne Hormann
Deposited On:06 Feb 2015 04:41
Last Modified:03 Oct 2019 07:49

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