ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
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
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.
Chemical Papers 64 (4) 499–503 (2010)