Effect of ionic liquids in unimolecular solvolysis reactions involving carbocationic intermediates
2014
Kochly, Elizabeth D. | Citrak, Susan | Gathondu, Nelius | Amberchan, Gabriella
Solvolysis studies of pivaloyl triflate were performed using ionic liquid/methanol solvent mixtures. The rearranged carbocation intermediate reacts with methanol via nucleophilic attack or elimination of a proton. Relative amounts of products were determined through ¹H NMR analysis. For most ionic liquids, increasing the ionic liquid:methanol ratio leads to increased yields of elimination product. Product ratios vary based on Kamlet–Taft solvatochromic parameters of hydrogen bond donating and accepting ability of the ionic liquid.
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