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

摘要: 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 five steps. Following acylation benzene with chloride, the resulting α-methylene group oxidized to 1,2-diketone three steps: successive bromination, substitution lithium hydroxide, and oxidation α-hydroxyketone potassium dichromate. The final step dehydrochlorination 4-chloro-1-phenyl-butane-1,2-dione. attempted copolymerization this styrene, using AIBN as initiator, unsuccessful.