Abstract
The electrochemical characteristics of 9-fluorenone have been investigated in various ionic liquids as a means of determining the extent of interaction of representative Lewis acids with this ketone. The ionic liquids studied, with Lewis acids in a particular medium, are : 1-ethyl-3-methylimidazolium tetrafluoroborate (EMI BF4) [BF3 etherate], 1-butyl-1-methylpyrrolidinium trifluoromethanesulfonate (BMPY TfO) [Hf(TfO)4 and Sc(TfO)3], and aluminum chloride : 1-ethyl-3-methylimidazolium chloride (AlCl3 : EMICl) [aluminum chloride]. In EMI BF4 and BMPY TfO, 9-fluorenone undergoes two successive one-electron transfers; however, addition of a Lewis acid produces a new reduction process shifted to a more positive potential. The extent of this shift is taken as an indication of the strength of the Lewis acid interaction with 9-fluorenone. The strongest Lewis acid : 9-fluorenone interaction, judging from the magnitude of the potential shift, is found in the AlCl3 : EMIC ionic liquid, followed by that of Hf(TfO)4 in BMPY TfO. The interaction of Sc(TfO)3 with 9-fluorenone in BMPY TfO is considerably less than that of Hf(TfO)4. In EMI BF4, however, Sc(TfO)3 interacts quite strongly with 9-fluorenone, indicating that the triflate anion interacts extensively enough with Sc3+ in BMPY TfO to restrict its complexation of 9-fluorenone.
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