The stepped reaction of decafluorobiphenyl with thiophenol studied by in situ 19F NMR spectroscopy

•Phenylthio-substituted perfluorobiphenyls were fully characterized by NMR spectroscopy.•Reaction kinetics was followed by in situ 19F NMR spectroscopy.•Almost exclusively even-numbered substitution pattern was observed.•Pseudo-first order rate constants were determined for two reaction steps.•Very pronounced differences in rate constants and reactivity were obtained.

Kinetic studies on the reaction of decafluorobiphenyl and di- and tetra(phenylthio)-substituted perfluorobiphenyl with thiophenol in the presence of triethylamine were performed by in situ 19F NMR spectroscopy to determine rate constants. In well-defined consecutive reactions, the even-numbered phenylthio derivatives are main products whereas the odd-numbered derivatives are much more reactive and were observed only in low concentrations. Very pronounced differences in rate constants and reactivity were obtained.

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