T. Akeng'a, R. Read
2005
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Journal
Bulletin of The Chemical Society of Ethiopia
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.