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Dibenzylideneacetone
Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C17H14O. It is a bright yellow solid insoluble in water, but soluble in ethanol. Dibenzylideneacetone is used as a sunscreen component and it is used as a ligand in organometallic chemistry for instance in tris(dibenzylideneacetone)dipalladium(0). In this case, it is a labile ligand which is easily displaced by stronger ligands like triphenylphosphine, hence it serves a useful entry point into palladium(0) chemistry. Additional recommended knowledgePreparationThe compound can be prepared in the laboratory by an aldol condensation of benzaldehyde and acetone with sodium hydroxide in a water / ethanol medium with the exclusive formation of the trans,trans isomer (melting point 107–111 °C).[1] This reaction is frequently encountered in organic chemistry education as a laboratory procedure. The conversion proceeds via the intermediacy of benzylideneacetone. Prolonged exposure to sunlight converts the compound in a [2+2] cycloaddition to a mixture of four cyclobutane isomers.[2] References
Categories: Ketones | Sunscreening agents |
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dibenzylideneacetone". A list of authors is available in Wikipedia. |