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Effect of ionic liquids in unimolecular solvolysis reactions involving carbocationic intermediates |
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| Affiliation: | 1. Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran;2. Laboratory of Physical Chemistry, Department of Chemistry, The University of Ioannina, 45110 Ioannina, Greece;1. Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kitaku, Okayama 700-8530, Japan;2. Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan;3. WPI-Advanced Institute for Materials Research, Tohoku University, Sendai 980-8577, Japan |
| Abstract: | 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. |
| Keywords: | Ionic liquid Solvolysis Carbocation Nucleophile |
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