
%0 Journal Article
%A Nimgirawath, S 
%A Ritchie, E 
%A Taylor, WC 
%T The synthesis of 1,4-diketones
%J Australian Journal of Chemistry
%D 1976/02/01
%V 29
%N 2
%P 339-356
%K 
%R https://doi.org/10.1071/CH9760339
%U https://www.publish.csiro.au/paper/CH9760339 
%X Recent methods for the synthesis of 1,4-diketones are briefly reviewed.Zinc and phenacyl bromide in dimethoxyethane afforded 1,4-diphenylbutane-l,4-dione in moderate yield, but other solvents or metals examined gave no or a lower yield. The route is unsatisfactoryfor aliphatic 1,4-diketones. Attempts to use 'levulinyl chloride' to acylate olefins or acetylenes were fruitless. Routes involving aldol condensations of hexane-2,5-dione or its monoacetal had very restricted success, as did those depending on the halogenolysis of acyl derivatives of phenacylmalonic ester. A fairly general route to 1,4-diketones was found in the sequence: valine to N-acylvaline to oxazol-5-one to Michael addition product with an &#945;, &#946;-unsaturated ketone followed by alkaline hydrolysis.The Michael addition is not regiospecific and valine derivatives may also be isolated. Yields of 1,4-diketones are only moderate but the synthesis is quick and convenient. 
