- Oxopropenylation of Alkylmagnesium Halides by 3-(Trimethylsilyloxy)acroleins
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Oxopropenylation of alkylmagnesium halides 4 by 3-(trimethylsilyloxy)acroleins 3 selectively yields the (E)-isomers of α,β-unsaturated aldehydes such as 4-phenyl-2-butenals 9, 3-cyclopropylpropenals 10, 3-cyclohexylpropenals 11, 3-(3-menthyl)propenals 12, and 2,5-hexadienals 13. 3-Hydroxyenolsilylethers 6 are isolated when allylmagnesium chloride is used as carbon nucleophile; to conclude, the reaction primarily involves nucleophilic addition of the Grignard reagent at the aldehyde carbon of the acrolein 3.
- Ullrich, Friedrich-Wilhelm,Rotscheidt, Klaus,Breitmaier, Eberhard
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p. 1737 - 1744
(2007/10/02)
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- ETHERS D'ENOLS β-CETONIQUES : SYNTHESE ET REACTIVITE VIS-A-VIS D'ORGANOLITHIENS.
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β-keto enol ethers substituted by ethyl group on carbon 2 are obtained by addition of lithium dimethylcuprate at low temperature on β-oxo α-methylene acetals; alcoholate elimination occurs during hydrolysis.Insaturated aldehydes are obtained by exclusive addition of organolithiocompounds on unhindered carbonyl group of β-keto enol ethers.
- Depezay, Jean-Claude,Saniere, Michele
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p. 1869 - 1876
(2007/10/02)
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