Author/Authors :
sabir, s. sidi mohamed ben abdallah university - faculty of sciences and techniques - laboratory of applied organic chemistry, Fez, Morocco , misbahi, k. sidi mohamed ben abdellah university - faculty of sciences and techniques - laboratory of applied organic chemistry, Fez, Morocco , rodi, y. kandri sidi mohamed ben abdellah university - faculty of sciences and techniques - laboratory of applied organic chemistry, Fez, Morocco , kholtei, a. moulay ismail university - faculty of science - laboratory of chemistry–biology applied to environment, Meknes, Morocco , essassi, e.m. rabat design center - moroccan foundation for advanced science, innovation and research (mascir), Rabat, Morocco , essassi, e.m. mohammed v university in rabat - faculté des sciences, urac 21, pôle de compétences pharmacochimie, centre de recherche des sciences des médicaments - laboratoire de chimie organique hétérocyclique, Rabat, Morocco
Abstract :
The reductive deshalogenation of cationic compounds (η^5-C5H5)Fe^+(η^6-halogenoarene) was investigated by cyclic voltammetry in organic solvents. In all cases,whatever the solvent or the substrate, the first reduction is a one-electron process leading tothe corresponding neutral species (η^5-C5H5)Fe(η^6-halogenoarene). In coordinating solvents(CH3CN, DMF) these species are involved in a competition between decomposition andhalide elimination. In CH2Cl2 or acetone the expected halide elimination of Cl- or Br- affordsthe deshalogenated compounds (η^5-C5H5) Fe^+(η^6-arene) after abstraction of hydrogen atom ofthe solvent by the intermediates (η^5-C5H5) Fe^+(aryl radical). It is suggested that theseintermediates are involved in decoordination occurring during the electrochemical reduction.For complexed monochloarenes, the yield of (η^5-C5H5)Fe^+(η^6-arene) increases with theelectrodonating effect of substituent. The observed competition between reductivedeshalogenation and decoordination throws light on the deshalogenation occurring during thepreparation of the substrates (η^5-C5H5)Fe^+(η^6-halogenoarene).
NaturalLanguageKeyword :
aromatic halogenated compounds , electrochemistry , reduction , cyclic voltammetry
