Journal Article α-exomethylene lactone possessing acetal–ester linkage: Polymerization and postpolymerization modification for water-soluble polymer

Kohsaka, Yasuhiro  ,  Matsumoto, Yusuke  ,  Zhang, Tianyi  ,  Matsuhashi, Yosuke  ,  Kitayama, Tatsuki

54 ( 7 )  , pp.955 - 961 , 2016-04-01 , WILEY
First published: 16 October 2015
2,6-Dimethyl-5-methylene-1,3-dioxa-4-one (DMDO), a cyclic acrylate possessing acetal–ester linkage, was obtained as a mixture of cis- and trans-isomers (95:5) from Baylis–Hillman reaction of an aryl acrylate. The radical and anionic polymerizations of DMDO yielded the corresponding vinyl polymers without any side reactions such as cleavage of the acetal–ester linkage. The polymerization behaviors were significantly different from that of the acyclic acrylate, α-(hydroxymethyl)acrylic acid, which was expected inactive against polymerization due to the steric hindrance around the vinylidene group by the α-substituent. The acetal–ester linkage of the obtained polymer (P1) was completely cleaved via acid hydrolysis to afford a water soluble polymer, P2. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 955–961

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