α,β‐Doppeldeprotonierte Nitroalkane: Super‐Enamine? Vorläufige Mitteilung

α,β‐Doubly deprotonated nitroalkanes: Super‐enamines? At temperatures between −90° and −78° both the α and β‐proton of 1‐aryl‐2‐nitro‐ethanes (1) are abstracted by n‐butyllithium to give the dilithio derivatives of 3. These turn out to be excellent nucleophiles combining with alkyl halides, aldehydes, ketones, and ω‐nitro styrenes at the β‐nitro carbon atom to give products of type 2. It is shown that 2‐nitro‐propane undergoes the same double deprotonation and can be coupled with benzaldehyde at one of the β‐nitro carbon atoms to yield 4. It is proposed to consider the new reagents as super‐enamines 3c.