Reagents and synthetic methods 41: oxidations with chromium trioxide under the influence of crown ethers

Abstract

M. JUARISTI, J. M. AIZPURUA. B. LECEA, and C. PALOMO. Can. J. Chem. 62, 2941 (1984). An unusual new application of crown ethers in organic synthesis is described. Chromium trioxide, in the presence of a crown ether as catalyst, in dichloromethane as solvent, was found an efficient oxidizing system for the chemoselectivc oxidation of mercaptans to disulfidcs. It is also highly efficient for the oxidation of hydroquinoncs to thc corresponding bcnzoquinoncs in almost quantitative yield. A high conversion of polynuclear hydrocarbons into quinones in acetic acid media is also briefly described.