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 ...
