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From 4-nitrotoluene and 4,4′-dinitrobibenzyl to E-4,4′-dinitrostilbene: an electrochemical approach

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Abstract

The dianions formed by the electroreduction of Z-O2NC6H4CH[double bond, length as m-dash]CHC6H4NO2, E-O2NC6H4CH[double bond, length as m-dash]CHC6H4NO2, O2NC6H4CH2–CH2C6H4NO2 or O2NC6H4CMeH–CMeHC6H4NO2, as well as the anion radical arising from 4-nitrotoluene, are stable, in the time scale of cyclic voltammetry (DMF + 0.10 M NBu4BF4). However, in the electrolysis time scale (from minutes to hours), only the dianion O2NC6H4CMeH–CMeHC6H4NO22− remains stable, since the reduced species, Z-O2NC6H4CH[double bond, length as m-dash]CHC6H4NO22−, O2NC6H4CH2–CH2C6H4NO22− or O2NC6H4Me˙, evolve to form the E-O2NC6H4CH[double bond, length as m-dash]CHC6H4NO22− dianion. This intermediate is recovered as the neutral species E-O2NC6H4CH[double bond, length as m-dash]CHC6H4NO2 with concomitant water reduction after the work-up with water, as demonstrated by combined electrolysis, cyclic voltammetry experiments, UV-spectroelectrochochemistry and theoretical calculations. Bulk electrolysis under optimized conditions (ACN + 0.10 M NBu4BF4) provides 40% and 67% isolated yields of E-4,4′-dinitrostilbene from 4-nitrotoluene and 4,4′-dinitrobibenzyl, respectively.

Graphical abstract: From 4-nitrotoluene and 4,4′-dinitrobibenzyl to E-4,4′-dinitrostilbene: an electrochemical approach

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Publication details

The article was received on 09 Jan 2018, accepted on 19 Mar 2018 and first published on 19 Mar 2018


Article type: Paper
DOI: 10.1039/C8NJ00131F
Citation: New J. Chem., 2018, Advance Article
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    From 4-nitrotoluene and 4,4′-dinitrobibenzyl to E-4,4′-dinitrostilbene: an electrochemical approach

    I. Gallardo, A. B. Gómez, G. Guirado, A. Lariño, M. Moreno, M. Ortigosa and S. Soler, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ00131F

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