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Chemical Papers

, Volume 64, Issue 4, pp 499–503 | Cite as

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

  • Branislav HusárEmail author
  • Ivan Lukáč
  • Štefan Chmela
  • Jean-Louis Canet
  • Yves Troin
Original Paper
  • 91 Downloads

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.

Keywords

1,2-diketones phenyl vinyl ketone benzil photodegradable polymer 

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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2010

Authors and Affiliations

  • Branislav Husár
    • 1
    • 2
    Email author
  • Ivan Lukáč
    • 1
  • Štefan Chmela
    • 1
  • Jean-Louis Canet
    • 2
  • Yves Troin
    • 2
  1. 1.Polymer InstituteSlovak Academy of SciencesBratislavaSlovak Republic
  2. 2.Laboratoire de Chimie des Hétérocycles et des GlucidesClermont UniversitéClermont-FerrandFrance

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