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Meisenheimer Rearrangement of Allyl N-Oxides as a Route to Initiators for Nitroxide-Mediated “Living” Free Radical Polymerizations

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Department of Chemistry, Texas A&M University, P.O. Box 300012, College Station, Texas 77842
Cite this: Macromolecules 1998, 31, 18, 6380–6382
Publication Date (Web):August 13, 1998
https://doi.org/10.1021/ma980216+
Copyright © 1998 American Chemical Society

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    2. Ryan R. Langeslay, Justin R. Walensky, Joseph W. Ziller, and William J. Evans . Reactivity of Organothorium Complexes with TEMPO. Inorganic Chemistry 2014, 53 (16) , 8455-8463. https://doi.org/10.1021/ic501034b
    3. Kai-Uwe Schoening, Walter Fischer, Stefan Hauck, Alexander Dichtl and Michael Kuepfert. Synthetic Studies on N-Alkoxyamines: A Mild and Broadly Applicable Route Starting from Nitroxide Radicals and Aldehydes. The Journal of Organic Chemistry 2009, 74 (4) , 1567-1573. https://doi.org/10.1021/jo802403j
    4. Craig J. Hawker,, Anton W. Bosman, and, Eva Harth. New Polymer Synthesis by Nitroxide Mediated Living Radical Polymerizations. Chemical Reviews 2001, 101 (12) , 3661-3688. https://doi.org/10.1021/cr990119u
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    6. Dekun Wang,, Xiangdong Bi, and, Zhe Wu. Convenient Synthesis and Application of a New Unimolecular Initiator. Macromolecules 2000, 33 (7) , 2293-2295. https://doi.org/10.1021/ma991546c
    7. Didier Benoit,, Eva Harth,, Peter Fox,, Robert M. Waymouth, and, Craig J. Hawker. Accurate Structural Control and Block Formation in the Living Polymerization of 1,3-Dienes by Nitroxide-Mediated Procedures. Macromolecules 2000, 33 (2) , 363-370. https://doi.org/10.1021/ma991187l
    8. Guowei Wang, Junlian Huang. Versatility of radical coupling in construction of topological polymers. Polym. Chem. 2014, 5 (2) , 277-308. https://doi.org/10.1039/C3PY00872J
    9. Julien Nicolas, Yohann Guillaneuf, Catherine Lefay, Denis Bertin, Didier Gigmes, Bernadette Charleux. Nitroxide-mediated polymerization. Progress in Polymer Science 2013, 38 (1) , 63-235. https://doi.org/10.1016/j.progpolymsci.2012.06.002
    10. Paola Astolfi, Lucedio Greci, Pierluigi Stipa, Corrado Rizzoli, Cedric Ysacco, Marion Rollet, Laurent Autissier, Antoine Tardy, Yohann Guillaneuf, Didier Gigmes. Indolinic nitroxides: evaluation of their potential as universal control agents for nitroxide mediated polymerization. Polymer Chemistry 2013, 4 (13) , 3694. https://doi.org/10.1039/c3py00368j
    11. Claude Commandeur, Malgorzata Commandeur, Kathell Bathany, Brice Kauffmann, Andrew J.F. Edmunds, Peter Maienfisch, Léon Ghosez. Study of the oxidation of 3-hydroxypyrroloindoles to pyrrolobenzoxazine alkaloids. Tetrahedron 2011, 67 (51) , 9899-9908. https://doi.org/10.1016/j.tet.2011.09.112
    12. . Meisenheimer Rearrangement. 2010https://doi.org/10.1002/9780470638859.conrr424
    13. L'ubica Búcsiová, Meizhen Yin, ŠTefan Chmela, Wolf D. Habicher. Nitroxide‐mediated Living Radical Polymerization of Styrene with Fluorescent Initiator. Journal of Macromolecular Science, Part A 2008, 45 (9) , 761-768. https://doi.org/10.1080/10601320802222897
    14. Qing Xia, Robert B. Grubbs. In situ generation of nitroxide from alkoxyamines for controlled acrylate polymerization. Journal of Polymer Science Part A: Polymer Chemistry 2006, 44 (17) , 5128-5136. https://doi.org/10.1002/pola.21605
    15. Bongjin Moon, Minhyuk Kang. Practical synthesis of alkoxyamine initiators for living radical polymerization. Macromolecular Research 2005, 13 (3) , 229-235. https://doi.org/10.1007/BF03219057
    16. T. Krause, W.D. Habicher, M. Messerschmidt, B.I. Voit. A novel method for the synthesis of alkoxyamine initiators for nitroxide-mediated radical polymerization using Mn(OAc)3 as electron-transfer reagent. Designed Monomers and Polymers 2004, 7 (4) , 391-397. https://doi.org/10.1163/1568555041475275

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