5-Hydroxy-2,3-dihydrobenzofuran-derived polyfunctional antioxidants 2. Synthesis of 2-dodecylselenomethyl-5-hydroxy-2,3-dihydrobenzofurans and their antioxidant profile versus 2-dodecylthiomethyl-substituted analogs

Abstract

A number of 2-dodecylselenomethyl-5-hydroxy-2,3-dihydrobenzofurans were synthesized from the corresponding 5-alkoxy-2-iodomethyl-substituted derivatives. The rate constants of the reaction with peroxide radicals and stoichiometric coefficients of inhibition were measured for the synthesized compounds and their 2-dodecylthiomethyl substituted analogs in the model reaction of initiated styrene oxidation. The dissociation energies of O–H bond were also calculated. 2-Dodecylselenomethyl-5-hydroxy-2,3-dihydrobenzofurans exceed their sulfurcontaining analogs and tocopherols by antioxidant activity in the thermal autooxidation of methyl oleate by a factor of 9–14 and 19–20, respectively.