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[摘要]：Mono- and bis(trifluoromethylthio)-substituted and perfluorooctanesulfonylferrocene derivatives were prepared by nucleophilic substitution reactions on the ferrocene core Thus Hg(SCF3)(2) was activated in situ by Cu and used for nucleophilic displacement reactions of bromide. Trifluoromethylsulfonylferrocene was not accessible by this method. The reaction of lithioferrocene with trifuloromethylsulfonyl chloride gave chloroferrocene ill small yield, presumably due to the high lattice energy of solid LiF. On the other hand, the known trifluoromethylferrocene was obtained as the only isolable compound from the photochemical reaction of CF3SSCF3, with ferrocene. The same product was detected in small amounts in the reaction of chloromercuryferrocene with trifluoromethylsulfonyl chloride. It thus appears that most established methods for trifluoromethylation of purely organic compounds fail for ferrocene due to Concurring redox reactions. The new compounds have been comprehensively characterized by elemental analyses, NMR and IR spectroscopy, mass spectrometry, and electrochemistry. The SCF3 group appears to be almost as electron-withdrawing as a trifluoromethyl group oil the ferrocene core. |
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