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α,β‐Doppeldeprotonierte Nitroalkane: Super‐Enamine? Vorläufige Mitteilung
Author(s) -
Henning Rainer,
Lehr Friedrich,
Seebach Dieter
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590634
Subject(s) - chemistry , deprotonation , nitro , medicinal chemistry , nucleophile , enamine , yield (engineering) , alkyl , nitroethane , benzaldehyde , reagent , aryl , carbanion , organic chemistry , catalysis , ion , materials science , metallurgy
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 .