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Licensed Unlicensed Requires Authentication Published by De Gruyter May 6, 2010

Synthesis of 1-phenylbut-3-ene-1,2-dione and its attempted radical polymerization

Branislav Husár EMAIL logo , Ivan Lukáč , Štefan Chmela , Jean-Louis Canet and Yves Troin
From the journal Chemical Papers

Abstract

1,2-Diketone moiety-bearing monomer 1-phenylbut-3-ene-1,2-dione, an analogue of phenyl vinyl ketone, was synthesized from 4-chlorobutyryl chloride in a 29 % overall yield in five steps. Following acylation of benzene with 4-chlorobutyryl chloride, the resulting α-methylene group was oxidized to 1,2-diketone in three steps: successive bromination, substitution with lithium hydroxide, and oxidation of α-hydroxyketone with potassium dichromate. The final step was dehydrochlorination of 4-chloro-1-phenyl-butane-1,2-dione. The attempted copolymerization of this monomer with styrene, using AIBN as the initiator, was unsuccessful.

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Published Online: 2010-5-6
Published in Print: 2010-8-1

© 2010 Institute of Chemistry, Slovak Academy of Sciences

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