Co-host: The Chemical Society of Japan, The Society of Synthetic Organic Chemistry, Japan (Cooperation)
The solvolysis of p-methoxyneophyl ester in ionic liquids was examined as the foundation that search for the useful organic reactions using the ionic liquids, and compared with the solvolysis in the standard molecular solvents. The reaction of p-fluorobenzensulfonate was followed by 19F-NMR and the rate of reaction was determined. The rate constants in [bmim][PF6] and [emim][BF4] are comparable to that in ethanol under buffer (2,6-dimethylpyridine) conditions, that is, the ionizing power is almost the same. The products and the thermodynamic parameter on rates indicate that the reaction mechanisms are SN1 and E1. It was suggested that presence of hydrogen at imidazolium ring 2nd position has influenced the rate constants of phenonium ion formation. In the ionic liquid, it was also confirmed that there are the additive effects, such as halogen and water, and there is the large catalyst effect by acid.
