Kinetics and mechanism of oxidation of aromatic secondary alcohols by Tl(III) acetate

Abstract

The kinetics of oxidation of ortho, meta and para substituted α-phenyl ethyl alcohols by Tl(III) shows that these reactions are susceptible to electronic influences. The negative ρ(−2·11) points to the formation of electron deficient carbon atom. The oxidation of benzhydrol exhibits a kinetic isotope effect 6·4. The Tl(III) oxidation of l-phenyl propyl alcohol, 4-chloro benzhydrol, 1-naphthyl methyl carbinol, 2-naphthyl methyl carbinol and fluorenol has been studied. A mechanism involving the loss of hydrogen atom as a hydride ion is proposed. The thermodynamic parameters of the reaction are also presented.