Dibenzylideneacetone
Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C17H14O. It is a pale-yellow solid insoluble in water, but soluble in ethanol. Dibenzylideneacetone is used as a component in sunscreens and as a ligand in organometallic chemistry.
It was first prepared in 1881 by the German chemist Rainer Ludwig Claisen and the Swiss chemist Charles-Claude-Alexandre Claparède.Preparation
The trans,trans isomer can be prepared in high yield and purity by condensation of benzaldehyde and acetone with sodium hydroxide in a water/ethanol medium followed by recrystallization.
This reaction, which proceeds via the intermediacy of benzylideneacetone, compound is often prepared in organic chemistry classes.Reactions and derivatives
Prolonged exposure to sunlight initiates cycloadditions, converting it to a mixture of a dimeric and a trimeric cyclobutane cycloadduct.
Dibenzylideneacetone is a component of the catalyst trisdipalladium. It is a labile ligand that is easily displaced by triphenylphosphine, hence it serves a useful entry point into palladium chemistry.
