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

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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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Authors and Affiliations

  1. Polymer Institute, Slovak Academy of Sciences, Dúbravská cesta 9, 842 36, Bratislava, Slovak Republic

    Branislav Husár, Ivan Lukáč & Štefan Chmela

  2. Laboratoire de Chimie des Hétérocycles et des Glucides, Clermont Université, B. P. 10448, ENSCCF, EA 987, 63000, Clermont-Ferrand, France

    Branislav Husár, Jean-Louis Canet & Yves Troin

Authors
  1. Branislav Husár
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  2. Ivan Lukáč
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  3. Štefan Chmela
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  4. Jean-Louis Canet
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  5. Yves Troin
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Correspondence to Branislav Husár.

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Husár, B., Lukáč, I., Chmela, Š. et al. Synthesis of 1-phenylbut-3-ene-1,2-dione and its attempted radical polymerization. Chem. Pap. 64, 499–503 (2010). https://doi.org/10.2478/s11696-010-0023-9

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  • DOI: https://doi.org/10.2478/s11696-010-0023-9

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