100789-77-3Relevant academic research and scientific papers
Oxopropenylation of Alkylmagnesium Halides by 3-(Trimethylsilyloxy)acroleins
Ullrich, Friedrich-Wilhelm,Rotscheidt, Klaus,Breitmaier, Eberhard
, p. 1737 - 1744 (2007/10/02)
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.
