Synthesis of 1-phenylbut-3-ene-1,2-dione and its attempted radical polymerization |
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Authors: | Branislav Husár Ivan Lukáč Štefan Chmela Jean-Louis Canet Yves Troin |
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Affiliation: | 1.Polymer Institute,Slovak Academy of Sciences,Bratislava,Slovak Republic;2.Laboratoire de Chimie des Hétérocycles et des Glucides,Clermont Université,Clermont-Ferrand,France |
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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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