Trimeric products from the free radical oxidation of (Z)-isoeugenol

Abstract

Four trimeric oxidation products have been isolated from the reaction between isoeugenol and tri-t-butylphenoxyl radical in methanol, and structures for these have been proposed on the basis of their proton magnetic resonance and mass spectral properties. All linkages were those expected from radical coupling, and one of the products was an acetal. Thus a route to the formation of ketones in lignin is demonstrated.