Phase-Transfer Nucleophilic Reactions Using Water-Insoluble Alcohols as Organic Solvents

Article abstract of DOI:10.1246/bcsj.68.2417

Simple nucleophilic substitutions were done under liquid-liquid phase-transfer reaction conditions using water-insoluble alcohols as organic solvents.The reactions proceeded at considerable rates even in the absence of any catalysts, depending on the alcohol, inorganic salt, and the aqueous concentration of the salts.An addition of single- or double-chained onium salts enhanced the reaction rate almost linearly with the amount of the onium salts.The concentrations of inorganic salts and water in the alcohol phase were analyzed and the relationship between these concentrations and the observed rate constant was discussed.An interfacial reaction mechanism explains the kinetics of this reaction system better than the conventional ion-pair mechanism assumed by most research using hydrocarbon solvents.