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Pàgina inicial > Articles > Articles publicats > From 4-nitrotoluene and 4,4'-dinitrobibenzyl to E -4,4'-dinitrostilbene : |
Data: | 2018 |
Resum: | 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. |
Ajuts: | Ministerio de Economía y Competitividad CTQ2012-30853 Ministerio de Economía y Competitividad CTQ2014-53144-P Ministerio de Economía y Competitividad CTQ2015-65439R |
Drets: | Tots els drets reservats. |
Llengua: | Anglès |
Document: | Article ; recerca ; Versió acceptada per publicar |
Publicat a: | New journal of chemistry, Vol. 42, Issue 9 (May 2018) , p. 7005-7015, ISSN 1369-9261 |
Postprint 12 p, 1.5 MB |