Kinetics and mechanism of oxidation of tri-n-butylstannyl alkoxides of benzhydrol and substituted benzhydrols by bromine in carbon tetrachloride

Article abstract of DOI:10.1016/0022-328X(88)80182-7

The tri-n-butylstannyl alkoxides (TBSA) of benzhydrols were prepared by treating the alcohols with tri-n-butyltin oxide (TBTO) and azeotropically removing the water.They were oxidised by bromine in carbon tetrachloride to the corresponding ketones.The oxidation was found to be a second order process.The effect of substituents on the rate was studied and the Hammett ρ was found to be -2.55 at 308 K.A mechanism is proposed.