Oxidation of a simple alkene by thallium(III) trifluoroacetate

Abstract

The oxidation of oct-1-ene by thallium(III) trifluoroacetate in a number of solvents has been studied. The initial organothallium adduct is stable under the reaction conditions used but on pouring into water it rapidly decomposes to give mainly octan-2-one, 1,2-epoxyoctane, and octane-1,2-diol. A feature of this decomposition is that a trifluoroacetoxy-substituent on C-2 is almost completely hydrolysed under conditions which leave octane-1,2-diol bistrifluoroacetate largely unchanged. It is suggested that the neighbouring thallium substituent aids hydrolysis, and a mechanism to account for this is proposed.