Methyltrioxorhenium: oxidative cleavage of CC-double bonds and its application in a highly efficient synthesis of vanillin from biological waste

An oxidation system consisting of methyltrioxorhenium and H2O2 catalyzes the cleavage of CC-double bonds. By varying the reaction conditions, it is possible to generate either the aldehyde or the carboxylic acid in reasonable-to-excellent yields and selectivities, depending on the starting material. The application of these findings to isoeugenol and trans-ferulic acid - both available from renewable resources - results in a highly efficient synthesis of vanillin. (C) 2000 Elsevier Science B.V. All rights reserved.