OLIGOMERIZATION MECHANISM OF CYCLOHEXENE OXIDE

Oligomerization of cyclohexene oxide was studied in the presence of tw o competitive nucleophiles (methanol and acetic acid). The resulting o ligomers, 2-methoxyl-2'-hydroxyl-dicyclohexyl ether (II) and 2-acetoxy l-2'-hydroxyl-dicyclohexyl ether (IV), were isolated and spectroscopic ally characterized. The formulation of these oligomers were evaluated as a function of the reactant molar ration, pH, and temperature. The r eaction 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 depe ndence on the concentration of cyclohexene oxide, and first order depe ndence on the nucleophile and proton concentration, respectively. The major reaction pathway proposed for the formation of the cyclohexene o xide 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). (C) 1998 Published by Elsevier Scie nce Ltd. All rights reserved.