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Catalyst-free click cascade functionalization of unsaturated-bond-containing polymers using masked-ketene-tethering nitrile N-oxide

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Title: Catalyst-free click cascade functionalization of unsaturated-bond-containing polymers using masked-ketene-tethering nitrile N-oxide
Authors: Cheawchan, Sumitra Browse this author
Koyama, Yasuhito Browse this author →KAKEN DB
Uchida, Satoshi Browse this author
Takata, Toshikazu Browse this author →KAKEN DB
Keywords: Nitrile N-oxide
Cascade functionalization
Catalyst-free grafting onto and cross-linking reaction
Issue Date: 2-Aug-2013
Publisher: Elsevier sci ltd
Journal Title: Polymer
Volume: 54
Issue: 17
Start Page: 4501
End Page: 4510
Publisher DOI: 10.1016/j.polymer.2013.06.020
Abstract: We developed a facile protocol for grafting-onto and cross-linking unsaturated-bond-containing common polymers via the formation of masked-ketene-functionalized polymers. The protocol utilizes a cascade functionalization agent 1 that has nitrile N-oxide and masked ketene functionalities. Through the model ligation reactions using 1, it turned out that the 1 facilitates the catalyst-free click introduction of masked ketene moieties to the unsaturated bonds such as C equivalent to N and C=C bonds, capable of undergoing catalyst-free ligation with not only a nucleophilic amine but also a neutral alcohol with low nucleophilicity. On the basis of these results, the catalyst-free grafting reactions of PEG onto EPDM and PAN using 1 were performed to afford the corresponding graft copolymers in excellent conversion yields. In addition, it was also revealed that heating of both PAN and NR with masked ketene moieties at 250 degrees C for 1 h without catalyst enables the efficient conversion to give the respective cross-linked polymers. (c) 2013 Elsevier Ltd. All rights reserved.
Type: article (author version)
URI: http://hdl.handle.net/2115/53275
Appears in Collections:触媒科学研究所 (Institute for Catalysis) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 小山 靖人

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