Summary.
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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Present address: Boron Molecular Pty. Ltd., P.O. Box 756, Noble Park, Victoria, Australia 3174 E-mail: cmoorhoff@boronmolecular.com
Received August 27, 2002; accepted September 3, 2002
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Moorhoff, C. Condensations of γ-Acetylacetonephosphonium Ylide (1-(Triphenylphosphoranylidene) pentane-2,4-dione) with Carbonyl Compounds. Monatshefte für Chemie 134, 429–434 (2003). https://doi.org/10.1007/s00706-002-0548-x
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DOI: https://doi.org/10.1007/s00706-002-0548-x