86659-50-9Relevant articles and documents
Oxidation by Cobalt(III) Acetate. Part 10. Effects of Ring Substituents on the Product Distributions in the Oxidation of β-Methylstyrenes by Cobalt(III) Acetate in Acetic Acid
Morimoto, Takashi,Hirano, Masao,Echigoya, Kohki,Sato, Takafumi
, p. 1205 - 1210 (2007/10/02)
The oxidation of ring-substituted β-methylstyrenes by cobalt(III) acetate in acetic acid has been studied by product analysis and the relative rates were measured by a competition method.Electron-releasing groups (p-MeO, pMe and p-But) accelerated both the reaction rate and the formation of glycol monoacetates, while electron-withdrawing groups (p-Cl and m-Cl) not only retarded the reaction but also favoured the formation of allylic acetate instead of glycol monoacetate.The good relationship of relative rates with ?+ in the Hammett plot showed that both products were derived from the same intermediate.The reaction mechanism is discussed in connection with the stabilities of radical cations formed by a one-electron transfer from the olefins to cobalt(III) acetate.
Electron-transfer Processes: Oxidation of α- and β-Alkenylbenzenes by Peroxydisulphate in Acetic Acid
Citterio, Attilio,Arnoldi, Claudio,Giordano, Claudio,Castaldi, Grasiano
, p. 891 - 896 (2007/10/02)
Oxidation of α- and β-unsaturated alkylbenzenes by peroxydisulphate in acetic acid gives side-chain acetoxylation with formation of the corresponding glycol diacetates and compounds (10), respectively.The reaction is catalysed by transition-metal salts, among which cupric acetate gives the best results.Generally, electron-releasing substituents on the benzene ring increase the yield and improve the selectivity.The same substrates are oxidized in water under Ag+ catalysis to the corresponding aldehydes.The different behaviour in the two solvents is ascribed to the difference in reactivity between the primary oxidation products and the starting olefin, whereas the initial oxidation step is suggested to occur in both cases via an electron-transfer process from the olefin to the sulphate radical anion.