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 .