Kinetic investigation in the formation of 2,2,5- trisubstituted tetrahydrofurans by catalyzed phenylselenoetherification of some terpenic alcohols

Abstract

The mechanism of the phenylselenoetherification of some naturally occurring alcohols linalool and nerolidol in the presence of some bases (piperidine, pyridine, triethylamine, quinoline) as catalysts was examined through the kinetic study of the cyclization under pseudo-first order conditions by UV-Vis spectrophotometry. It was demonstrated that the intramolecular cyclization is facilitated in the presence of some bases caused by the hydrogen bond between base and OHgroup of the alkenol. The obtained values for the rate constants show that there is a good agreement between those constants and the basicity of the catalyst. The fastest reaction is the one using the strongest base (piperidine) and the smallest rate constant corresponded to the use of the weakest base (quinoline). © 2013 Akadémiai Kiadó, Budapest, Hungary.