54826-18-5Relevant academic research and scientific papers
Quantitative estimation of the reactivity of perfluorinated methylbenzenes and benzocycloalkenes in nucleophilic substitution reactions
Rodionov, Peter P.,Osina, Ol'Ga I.,Platonov, Vyacheslav E.,Yakobson, Georg G.
, p. 986 - 993 (2007/10/02)
The kinetics of the reactions of perfluorinated xylenes, mesitylene, p-cymene, benzocycloalkenes (benzocyclobutene, indane, tetralin) and octafluoronaphthalene with sodium methoxide and piperidine have been studied.Rate constants of the reactions of perfluorinated aromatic compounds with sodium methoxide (taking into account one reaction centre) are shown to incease in the order: hexafluorobenzene perfluoro-p-xylene ca.= perfluoro-p-cymene octafluorotoluene ca.= perfluoro-m-xylene perfluoromesitylene ca.= perfluoro-o-xylene.In the reactions with piperidine, a different sequence was observed: hexafluorobenzene perfluoro-p-xylene perfluoro-p-cymene perfluoromesitylene perfluoro-m-xylene octafluorotoluene perfluoro-o-xylene.In the reactions of perfluorobenzocycloalkenes with sodium methoxide and piperidine, the reactivity grows by about a factor of 2 with increase of the perfluoroalicyclic ring size by one CF2-group, in the following order: perfluorobenzocyclobutene perfluoroindan perfluorotetralin.
