TY - JOUR
T1 - Mechanistic studies on the reactivity of halodinitrobenzene radical-anion
AU - Gallardo, Iluminada
AU - Guirado, Gonzalo
AU - Marquet, Jordi
PY - 2000/6/30
Y1 - 2000/6/30
N2 - The electrochemical behaviour of 1-F-2,4-dinitrobenzene, 1-Cl-2,4-dinitrobenzene and 1-Br-2,4-dinitrobenzene in DMF is described. The 1-F-2,4-dinitrobenzene radical anion dimerizes before cleaving, whereas 1-Cl-2,4-dinitrobenzene and 1-Br-2,4-dinitrobenzene radical anions dimerize after cleavage. This change in mechanism allows the obtention of 2,2′,4,4′-tetranitrobiphenyl in a selective way, and with good efficiency. The electrochemical oxidation of σ-complexes is shown to be an alternative means of obtaining products that are difficult to obtain through traditional procedures.
AB - The electrochemical behaviour of 1-F-2,4-dinitrobenzene, 1-Cl-2,4-dinitrobenzene and 1-Br-2,4-dinitrobenzene in DMF is described. The 1-F-2,4-dinitrobenzene radical anion dimerizes before cleaving, whereas 1-Cl-2,4-dinitrobenzene and 1-Br-2,4-dinitrobenzene radical anions dimerize after cleavage. This change in mechanism allows the obtention of 2,2′,4,4′-tetranitrobiphenyl in a selective way, and with good efficiency. The electrochemical oxidation of σ-complexes is shown to be an alternative means of obtaining products that are difficult to obtain through traditional procedures.
U2 - 10.1016/S0022-0728(00)00189-3
DO - 10.1016/S0022-0728(00)00189-3
M3 - Article
SN - 0022-0728
VL - 488
SP - 64
EP - 72
JO - Journal of Electroanalytical Chemistry
JF - Journal of Electroanalytical Chemistry
IS - 1
ER -