
TY  - JOUR
A1  - Nimgirawath, S 
A1  - Ritchie, E 
A1  - Taylor, WC 
T1  - The synthesis of 1,4-diketones
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1976
VL  - 29
IS  - 2
SP  - 339
EP  - 356
KW  - 
UR  - https://doi.org/10.1071/CH9760339 
N2  - 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. 
ER  -

