<b>Reactions of 5-[1-(2-phenyl)methylidene]-3-phenylimidazolidine-2,4-diones with some organometallic reagents</b>

• Main Authors: Teresa A. R. Akeng'a, Roger W. Read
• Format: Article
• Language: English
• Published: Chemical Society of Ethiopia 2005-06-01
• Series: Bulletin of the Chemical Society of Ethiopia
• Subjects: Imidazolidine-2; 4-diones; &alpha; beta; -Unsaturated carbonyl compounds; 1; 2-Addition; conjugate addition; Grignard reagents; Lithium dibutylcuprate
• Online Access: http://www.ajol.info/index.php/bcse/article/view/21109

The reaction of Grignard reagents with 5-[1-(2-chlorophenyl)methylidene]-3-phenylimidazolidine-2,4-dione, <b>4</b>, and 5-[1-(2-bromophenyl)methylidene]-3-phenylimidazolidine-2,4-dione, <b>5</b>, gave exclusively 1,2-addition products, <b>6-8</b>, in 70-80% yields. Lithium dibutylcuprate reacted with <b>4</b> to yield exclusively 1,2-addition product <b>9</b> (92%). No conjugate or 1,4-addition products were obtained. These results indicate that 5-[1-(2-phenyl)methylidene]-3-phenylimidazolidine-2,4-diones do not react like normal unsaturated carbonyl compounds.