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 .