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Issue 46, 2013
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Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO

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Abstract

Nitroolefins are usually synthesized using the Henry reaction. Here we report an alternative metal-free decarboxylative nitration protocol for the preparation of the nitroolefins from α,β-unsaturated carboxylic acids using t-butylnitrite (t-BuONO) and TEMPO. α,β-Unsaturated carboxylic acids bearing β-aromatic and β-heteroaromatic substituents gave (E)-nitroolefins exclusively under mild conditions. A radical based pathway has been proposed for this decarboxylative nitration reaction.

Graphical abstract: Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO

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Publication details

The article was received on 01 Mar 2013, accepted on 17 Apr 2013 and first published on 19 Apr 2013


Article type: Communication
DOI: 10.1039/C3CC41576G
Citation: Chem. Commun., 2013,49, 5286-5288
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    Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO

    S. Manna, S. Jana, T. Saboo, A. Maji and D. Maiti, Chem. Commun., 2013, 49, 5286
    DOI: 10.1039/C3CC41576G

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