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

  • Teresa A. R. Akeng'a<sup>1</sup>* <sup>1</sup>Department of Chemistry, JKUAT, P.O. Box 62000, Nairobi, Kenya
  • Roger W. Read<sup>2</sup> <sup>2</sup>School of Chemistry, University of New South Wales, 2052 Sydney, Australia
Keywords: Imidazolidine-2, 4-diones, a, b-Unsaturated carbonyl compounds, 1, 2-Addition, conjugate addition, Grignard reagents, Lithium dibutylcuprate

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.
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Articles

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eISSN: 1726-801X
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