ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

Branislav Husár, Ivan Lukáč, Štefan Chmela, Jean-Louis Canet, and Yves Troin

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

E-mail: branislav.husar@savba.sk

Received: 22 September 2009  Revised: 9 December 2009  Accepted: 12 December 2009

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

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-010-0023-9

Chemical Papers 64 (4) 499–503 (2010)