MN(VII) OXIDATION USING CETYLTRIMETHYLAMMONIUM PERMANGANATE - SELF-OXIDATION OF CTAP AND OXIDATION OF BENZYL ALCOHOL

Cetyltrimethylammonium permanganate (CTAP) has been prepared and characterized from IR and NMR data. At room temperature the compound is stable when kept in dark but at 115 degrees C it undergoes a violent thermal decomposition. In different organic solvents self-oxidation takes place giving rise to pentadecanal. The rate of self-oxidation in different solvents are in the order: benzonitrile > benzene > chloroform > carbon tetrachloride. A mechanism involving proton transfer from the beta-methylene group to the permanganate ion, thereby forming an olefinic intermediate, has been suggested. The oxidation kinetics of benzyl alcohol have been studied in chloroform medium. The thermodynamic parameters for the oxidation reactions have been evaluated. (C) 1995 John Wiley and Sons, Inc.