Mechanistic studies on the reactivity of halodinitrobenzene radical-anion

Iluminada Gallardo; Gonzalo Guirado; Jordi Marquet

doi:10.1016/S0022-0728(00)00189-3

Mechanistic studies on the reactivity of halodinitrobenzene radical-anion

Iluminada Gallardo, Gonzalo Guirado, Jordi Marquet

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

27 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	64-72
Journal	Journal of Electroanalytical Chemistry
Volume	488
Issue number	1
DOIs	https://doi.org/10.1016/S0022-0728(00)00189-3
Publication status	Published - 30 Jun 2000

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title = "Mechanistic studies on the reactivity of halodinitrobenzene radical-anion",

abstract = "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.",

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AU - Guirado, Gonzalo

AU - Marquet, Jordi

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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

VL - 488

SP - 64

EP - 72

IS - 1

ER -

Mechanistic studies on the reactivity of halodinitrobenzene radical-anion

Abstract

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