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European Journal of Organic Chemistry

European Journal of Organic Chemistry

IF: 2.5
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Ionic‐Liquid Controlled Nitration of Double Bond: Highly Selective Synthesis of Nitrostyrenes and Benzonitriles

Published:8 October 2020 DOI: 10.1002/ejoc.202001027
Michele Casiello , Daniela Caputo , Caterina Fusco , Pietro Cotugno , Vito Rizzi , Maria Michela Dell'Anna , Lucia D'Accolti , Angelo Nacci

Abstract

Unprecedented in literature, the conversion of aryl alkenes into β‐nitrostyrenes (2) or benzonitriles (3) with sodium nitrite can be governed by an appropriate choice of ionic liquid (IL) medium. A general trend was found for the selectivity of these processes, which depends on the nature of IL, with imidazolium‐based ILs, such as [Bmim]Cl, that favor the C–H nitration leading to β‐nitrostyrenes, while tetraalkylammonium‐based ILs, such as TBAA, privilege the C=C bond cleavage affording benzonitriles. Besides a substrate scope, mechanistic hypotheses were provided on the origin of the different selectivity in the two kinds of ILs, based on their own tunable properties such as polarity, viscosity, and solvent cage effects.

Synthesis

α-Methylcinnamaldehyde
1-Phenyl-2-nitropropene

Substances (2)

Related products
Procduct Name CAS Molecular Formula Supplier Price
Sodium nitrite 7632-00-0 NaNO2 927 suppliers $14.00-$2710.00
tert-Butyl acetoacetate 1694-31-1 C8H14O3 440 suppliers $6.00-$5880.00

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