DOI: 10.5176/2339-5060_1.1.5
Authors: Elizabeth D. Kochly, Todd Rabkin Golden and Seham Afaghani
Abstract:
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 phenomenon.
Keywords: carbocaction, ionic liquid, nucleophilicity, solvolysis
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