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DOI: 10.1055/s-0032-1317879
Ethyl 2-Diazoacetoacetate
Publication History
Publication Date:
08 January 2013 (online)
Introduction
α-Diazocarbonyl compounds have attracted great attention because of their versatile, synthetically useful transformations.[ 1 ] Their most important reactions are those that involve loss of molecular nitrogen induced by thermolytic, catalytic, and photolytic conditions.[1] [2] []
Conventional synthetic methods for diazo carbonyl compounds include diazotization of amines, dehydrogenation of hydrazones and diazo transfer reactions.[ 3 ] The diazo transfer donor is invariably a sulfonyl azide such as tosyl azide, p-carboxylbenzenesulfonyl azide, p-dodecylbenzenesulfonyl azide and methanesulfonyl azide. This Spotlight focusses on ethyl diazoacetatoacetate, a yellow oil (1.131 g/mL at 25 °C).[ 3 ] The general method for the construction of this reagent involves diazo-transfer reaction to the α-methylene position of ethyl acetoacetate in the presence of a base such as Et3N.[ 4 ]
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