The reaction of sodium cyclopentadienide was studied with three mono-halogenated models: 4-chloro-diphenylsulforie, 4-fluorobenzophenone and 4-chloro-trifluorotoluene. In spite of the absence of mobile hydrogen atoms in their structures, the reaction of these substrates with cyclopentadienide carbanion leads to a mixture of dienes di or trisubstituted and some of their dimmers obtained by Diels-Alder reaction which are identified by Gas Chromatographic/ MS coupling (GC-MS) and Liquid Secondary Ton Mass Spectrometry (LSIMS). A mechanistic interpretation was proposed for each case.
O. Mzani, H. Ben Romdhane, M. Baklouti
biscyclopentadienes, cyclopentadienide, nucleophilic aromatic substitution.