EFFECT OF REACTION MEDIUM ON DEHYDROGENATIVE POLYMERIZATION OF SINAPYL ALCOHOL

To investigate the effect of a reaction medium on dehydrogenative poly merization, sinapyl alcohol was reacted at various polarities and pHs of solvents. One-electron-oxidations were conducted inorganically and enzymatically by FeCl3 and horseradish peroxidase with H2O2, respectiv ely, as an oxidant. Dimers were separated from the products and analyz ed for their chemical structures. In the results, syringylglycerol-bet a-sinapyl alcohol ether was predominantly produced by FeCl3 with incre ases of dioxane content or acidity of the reaction medium. This phenom enon could be explained by the suppression of the E-effect (electron r elease) and by the action of the I-effect (electron induction) of meth oxyl groups in low polarity and low pH. However, syringaresinol occurr ed in large yields under any condition when peroxidase/H2O2 was used a s an oxidant. These results suggest that a difference between oxidatio ns of sinapyl alcohol with enzymatic and inorganic oxidants exists.