Effect of the Ionic Liquid 1-Butyl-3- Methylimidazolium Bistrifluoromethane- Sulfonamide on Nucleophile Reactivity in Unimolecular Solvolysis Reactions Involving Carbocationic Intermediates

Elizabeth D. Kochly, Todd Rabkin Golden, Seham Afaghani


Solvolysis studies of pivaloyl triflate were carried
out in the ionic liquid 1-butyl-3-methylimidazolium
bistrifluoromethanesulfonamide with various cosolvents.
Reaction solutions were analyzed by 1H NMR and the relative
amounts of substitution and elimination products measured. It
was found that regardless of cosolvent, increasing the ionic
liquid:cosolvent ratio leads to increased elimination product.
The rate of increase, however, is dependent on the identity of the
cosolvent. Kamlet-Taft solvatochromic parameters of hydrogen
bond accepting and donating ability were invoked to explain this


carbocaction, ionic liquid, nucleophilicity, solvolysis

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