Condensations of γ-Acetylacetonephosphonium Ylide (1-(Triphenylphosphoranylidene) pentane-2,4-dione) with Carbonyl Compounds |
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Authors: | Cornelis M Moorhoff |
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Abstract: | 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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