Hydroxylation and mechanistic studies of α, β-unsaturated compounds with alkaline hexacyanoferrate (III)

Abstract

The reactions of three α, β-unsaturated compounds of the type CH₂=CHX (where X = -CN, -CONH₂ and -C0₂ -) with alkaline hexacyanoferrate (III) have been studied. The reactions take place according to the rate expression, d[Fe(CN)₆^3-] / dt = k [Fe(CN)₆^3-) (CH₂=CHX] (OH^-). The values of k at 318K are 7.2 x 10^-4,4.45 X 10^-4 and 3.2 x 10^-4(dm⁶mol^-2s^-1) in the oxidations of the respective substrates. The oxidation rates follow the order: -CN> -CONH₂ > -C0₂ The substrates are oxidized to give diols under kinetic conditions. Tentative reaction mechanism leading to the formation of oxidation products has been suggested.