From 4-nitrotoluene and 4,4'-dinitrobibenzyl to E -4,4'-dinitrostilbene : An electrochemical approach
Gallardo, Iluminada (Universitat Autònoma de Barcelona)
Gómez, Ana Belén (Universitat Autònoma de Barcelona)
Guirado López, Gonzalo (Universitat Autònoma de Barcelona)
Lariño, Adrián (Universitat Autònoma de Barcelona)
Moreno Ferrer, Miquel (Universitat Autònoma de Barcelona)
Ortigosa, Manuel (Universitat Autònoma de Barcelona)
Soler, Sergio (Universitat Autònoma de Barcelona)

Date:	2018
Abstract:	The dianions formed by electroreduction of Z-O2NC6H4CH=CHC6H4NO2, E-O2NC6H4CH=CHC6H4NO2, O2NC6H4CH2-CH2C6H4NO2 or O2NC6H4CMeH-CMeHC6H4NO2, as well as the anion radical arising from 4-nitrotoluene are stable, in the time scale of the cyclic voltammetry (DMF+0. 10 M NBu4BF4). However, in the electrolysis time scale (from minutes to hours), only the dianion O2NC6H4CMeH-CMeHC6H4NO2 2- remains stable, since the reduced species, Z-O2NC6H4CH=CHC6H4NO2 2-, O2NC6H4CH2-CH2C6H4NO2 2- or O2NC6H4Me-, evolve to form the E-O2NC6H4CH=CHC6H4NO2 2- dianion. This intermediate, is recovered as the neutral species E-O2NC6H4CH=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 in optimized conditions (ACN+0. 10 M NBu4BF4) provides 40% and 67 % isolated yield of E-4,4'-dinitrostilbene from 4-nitrotoluene and 4,4'-dinitrobibenzyl, respectively.
Grants:	Ministerio de Economía y Competitividad CTQ2012-30853 Ministerio de Economía y Competitividad CTQ2014-53144-P Ministerio de Economía y Competitividad CTQ2015-65439R
Rights:	Tots els drets reservats.
Language:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Published in:	New journal of chemistry, Vol. 42, Issue 9 (May 2018) , p. 7005-7015, ISSN 1369-9261

DOI: 10.1039/c8nj00131f

Postprint 12 p, 1.5 MB

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Research literature > UAB research groups literature > Research Centres and Groups (research output) > Experimental sciences > Group in Electrochemistry, Photochemistry and Organic Reactivity (GEFRO)
Articles > Research articles
Articles > Published articles