Oxidative cross coupling of p-hydroxycinnamic alcohols with dimeric arylglycerol β-aryl ether lignin model compounds. The effect of oxidation potentials

Abstract

Oxidation of p-hydroxycinnamyl alcohols together with dimeric lignin model compounds containing arylglycerol β-aryl ether structures was found, under certain conditions, to yield cross coupling products with β-aryl ether and 5,5′-biphenyl bonds. Cross coupling appeared to be restricted to phenols of similar oxidation potential. The implications of the “limits to randomness” for the understanding of the lignification process in vascular plants are discussed.