Synthesis of dimethylsilyl bis-enol ethers derived from aldehydes.

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概要

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• Two procedures for the prepation of dimethylsilyl bis-enol ethers from aldehydes, through enolization, are described. Dimethylsilyl bis-enol ethers, derived from propanal, butanal, 2-methylpropanal, pentanal, hexanal, and heptanal have been synthesized by refluxihg a mixture of triethylamine, dichlorodimethylsilane and the corresponding aldehyde in tetrahydrofuran for 18–38 h. The yields are in the range of 75–90%. Alternatively, a stronger base, lithium 2,2,6,6-tetramethylpiperidide (LiTMP) is used for deprotonation of the above mentioned aldehydes at −23°C. The enolates are then quenched with dichlorodimethylsilane. The small aldehydes, propanal, butanal, and 2-methylpropanal fail to give the desired products, while the others gave a very good yields (56–85%). Ethanal fails to give the product in either of the two procedures. A competitive rate of polymerization with the rate of proton abstraction or with the rate of mixing of the reactants could explain these failures. The silyl bis-enol ethers have been characterized on the basis of their NMR, IR, and elemental analysis data.

• 公益社団法人 日本化学会の論文

著者

• Ibrahim M.

  Department Of Botany Faculty Of Science Suez Canal University

• Abdel-Rahman H.

  Department of Chemistry, Yarmouk University

• Fataftah Z.

  Department of Chemistry, Yarmouk University

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• Synthesis of dimethylsilyl bis-enol ethers derived from aldehydes.

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