Condensations of γ-Acetylacetonephosphonium Ylide (1-(Triphenylphosphoranylidene) pentane-2,4-dione) with Carbonyl Compounds

被引:0
作者
Cornelis M. Moorhoff
机构
[1] Department of Chemistry,
[2] University of Tasmania,undefined
[3] GPO Box 252-75C,undefined
[4] Hobart,undefined
[5] Tasmania,undefined
[6] Australia 7001,undefined
来源
Monatshefte für Chemie / Chemical Monthly | 2003年 / 134卷
关键词
Keywords. γ-Acetylacetonephosphonium ylide; 1-(Triphenylphosphoranylidene)pentane-2,4-dione; Unsaturated 2,4-diketone; 4-Hydroxy-2-oxo-3,5-diene; 4-Hydroxy-2-oxo-3,5,7-triene; Michael Wittig condensation.;
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摘要
2,4-Dioxopentyltriphenylphosphonium bromide reacted with aqueous sodium hydrogencarbonate in dichloromethane to give, in almost quantitative yield, 1-(triphenylphosphoranylidene) pentane-2,4-dione. Dianion Wittig- and Michael Wittig condensations of the last mentioned phosphonium ylide with carbonyl compounds gave unsaturated 2,4-diketones which were almost totally enolised in deutero chloroform as 4-hydroxy-2-oxo-3,5-dienes (24–70% yields). These products closely resembled the type of compounds derived from similar condensations with alkyl 3-oxo-4-(triphenylphosphoranylidene)butanoate.
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页码:429 / 434
页数:5
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