REACTIONS OF 5-[1-(2-PHENYL)METHYLIDENE]-3-PHENYLIMIDAZOLIDINE-2,4-DIONES WITH SOME ORGANOMETALLIC REAGENTS

Abstract

The reaction of Grignard reagents with 5-[1-(2-chlorophenyl)methylidene]-3-phenylimidazolidine-2,4-dione, 4, and 5-[1-(2-bromophenyl)methylidene]-3-phenylimidazolidine-2,4-dione, 5, gave exclusively 1,2-addition products, 6-8, in 70-80% yields. Lithium dibutylcuprate reacted with 4 to yield exclusively 1,2-addition product 9 (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.



KEY WORDS: Imidazolidine-2,4-diones, a,b-Unsaturated carbonyl compounds, 1,2-Addition, conjugate addition, Grignard reagents, Lithium dibutylcuprate


Bull. Chem. Soc. Ethiop. 2005, 19(1), 55-60.