Oligomerization of cyclohexene oxide was studied in the presence of two competitive nucleophiles (methanol and acetic acid). The resulting oligomers, 2-methoxyl-2＇-hydroxyl-dicyclohexyl ether (II) and 2-acetoxyl-2＇-hydroxyl-dicyclohexyl ether (IV), were isolated and spectroscopically characterized. The formulation of these oligomers were evaluated as a function of the reactant molar ration, pH, and temperature. The reaction rate constants, and Arrhenius parameters for the formation of the oligomers were determined over a pH range of 4 to 7. The reaction rates for the formation of the oligomers exhibited a second order dependence on the concentration of cyclohexene oxide, and first order dependence on the nucleophile and proton concentration, respectively. The major reaction pathway proposed for the formation of the cyclohexene oxide oligomers was via an activated chain end complex. The propagation of the activated chain end complex was then terminated by nucleophile attack (methanol or acetic acid).