Mn(VII) oxidation using cetyltrimethylammonium permanganate: Self‐oxidation of CTAP and oxidation of benzyl alcohol

Abstract

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°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 P-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. 0

The first step of oxidation of alkylbenzenes by permanganates in acidic aqueous solutions

“…The KIE values for the attack on the C--H bond by the three species are close, as in the case of alkanes3, 38,50 k_CH/k_ cD = koCH/ko cO = k+CH/k+ cB. (16) 2. Oxidation involving the benzene ring with each of the three Mn vH species has a KIE equal to 1.…”

“…ammonium salts, 13,14 crown etherslS), or in oNanic media in which tetraalkylammonium permanganates are soluble. [15][16][17] However, in each case, the process is complicated either by oxidation of the alkyl groups in R4NMnO 4 lfi or by oxidation of the solvent. 13,t4…”

Kinetic study of the oxidation of benzaldehyde by quaternary ammonium permanganates in dichloromethane solutions

“…However, the rate of the oxidation by cetyl trimethylammonium permanganate is much greater than the rates of the oxidation with other permanganate salts used. It is probable that the behavior of this reactant reflects its self-oxidation as reported in [6]. Negative values of the activation entropies indicate the fact that the activated complex is more organized than the initial state.…”

“…However, the solutions of permanganate are of limited stability due to the reaction of permanganate with the solvent [4,5]. In some cases the self-oxidation of the quaternary ammonium cation takes place, too [6]. The reaction product of permanganate was mistakenly identified in the past as a cyclic manganate(V) diester [7,8].…”

Three Reagents In One: Ammonium Permanganate In The Oxidation Of Benzyl Alcohol

“…Benzyl alcohol and its ring-substituted derivaives can be easily oxidized by various permanga nates [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. Reaction conditions, such as the najure of the oxidant and the medium, temperature, lie.…”