Solvated proton with ether, reaction

This is followed by solvation with diethyl ether molecules to yield Fe[(C2H5)20]2Cl. Diethyl molecules may become protonated by reaction with oxonium ions ... 

Much kinetic work has been done on the reaction of diphenyldiazo-methane with weak acids, HA (mainly carboxylic acids), in ethanol or toluene solutions [214, 216]. In these studies, catalysis by solvated protons is negligible in ethanol and non-existent in toluene. The reaction is first-order in diphenyldiazomethane and first-order in weak acid, HA. Reaction products in ethanol are benzhydryl ethyl ether (Ph2 CHOEt) and benzhydryl ester (Ph2 CHA). The only product in toluene is benzhydryl ester. The product ratio of the reaction in ethanol is insensitive to the addition of salts of the weak acid, and it is almost independent of the chemical nature of HA [216]. The solvent isotope effect in the reaction with benzoic acid in ethanol is (fenAktoH/ Da)eiod = 3.5. 

Thus, the differences in activities of protonic acids are due to the quality of the corresponding anion or to its tendency to form chemical bonds with the carbon cation. If the anion is unable to form such bonds without extensive regrouping or decomposition, the addition of the proton is followed by polymerization. Should the reactivity of the anion be suppressed by solvation, the tendency to polymerize is enhanced. Consequently, the efficiencies of protonic acids depend very much upon the polarities of the media and upon the reaction conditions [12, 13]. Also, the stronger the protonic acid the higher the reaction rate and the resultant degree of polymerization [14]. Generally, hydrogen halide acids do not initiate polymerizations of alkyl-substituted olefins. They may, however, initiate polymerizations of aryl-substituted olefins and vinyl ethers in polar solvents. The same is true of sulfuric acid [15]. 

---