Mechanistic studies on the electrochemical reductive coupling of some polyhalogenonitrobenzenes. A new example of a radical anion dimerization

Claude P. Andrieux, Anna Batlle, Martirio Espín, Iluminada Gallardo, Ziqi Jiang, Jorge Marquet

Research output: Contribution to journalArticleResearchpeer-review

15 Citations (Scopus)

Abstract

Coupling processes with loss of one halogen atom per ring are observed when heavily substituted polyhalogenonitrobenzenes (polyfluoro- and polychloro-) are electrochemically reduced in DMF. Product analyses and cyclic voltametry mechanistic studies suggest that in the particular case of pentafluoronitrobenzene, direct dimerization of the radical anions occurs prior to CF bond fragmentation. On the contrary, reduction of the nitro group is the only observed process when less substituted polyhalogenonitrobenzenes are used in the same conditions. Nitro group reduction is also the main process for all the studied polyhalogenonitrobenzenes when the reactions are carried out in protic solvents. © 1994.
Original languageEnglish
Pages (from-to)6913-6920
JournalTetrahedron
Volume50
Issue number23
DOIs
Publication statusPublished - 1 Jan 1994

Keywords

  • Dimerization
  • Fluoronitroaromatics
  • Reductive Coupling. Radical Anions

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