The Journal of Organic Chemistry

Reaction of. alpha.-azido esters with lithium ethoxide: synthesis of dehydroamino esters and. alpha.-keto esters

PA Manis, MW Rathke

Index: Manis, Paul A.; Rathke, Michael W. Journal of Organic Chemistry, 1980 , vol. 45, # 24 p. 4952 - 4954

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Citation Number: 46

Abstract

In an attempt to prepare enolate 1, ethyl 2-azidopropanoate was added to a solution of lithium diisopropylamide (LDA) in tetrahydrofuran (THF) at dry ice temperature. Nitrogen was evolved and the reaction mixture turned deep red. Hydrolytic workup gave an intractable tar and no GLC volatile products. Presumably, 1 is formed but spontanttously loses nitrogen to form imine anion 2, which, in the strongly basic reaction medium, undergoes further ...

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