10.1002/(SICI)1521-3765(19980710)4:7<1169::AID-CHEM1169>3.0.CO;2-H
The research study on the reaction between the [CpFe(CO)2]- anion and pentafluorochlorobenzene, aiming to understand the mechanism of nucleophilic aromatic substitution via a halogen-metal exchange process. The study concludes that the reaction does not follow a traditional S_N2Ar mechanism, but instead involves the formation of pentafluorophenyl carbanions, with the key step being the halogen-metal exchange. The reaction yields various products, including [C6F5Fe(CO)2Cp], chloroperfluoropolyphenyls, and [CpFe(CO)2]-, with the distribution influenced by factors such as the reactant ratio, solvent, counterion, and temperature. The research also involved the use of radical and carbanionic traps to control the reaction pathway and the counterions K+, K+-18-crown-6, and [(C2H5)2P-N=P(C2H5)2]+ (PPN+).