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The only detectable product obtained from the oxidation of cyclobutanol by ruthenium tetroxide or sodium ruthenate is cyclobutanone. This indicates that both of these reagents act as two-electron transfer oxidants and that the oxidation of alcohols by ruthenium tetroxide likely proceeds via a mechanism that involves a pair of successive two-electron transfer steps.

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The oxidation of 2-propanol and cyclobutanol by stoichiometric amounts of sodium ruthenate has been studied. Contrary to previously published speculations, it has been found that these reactions are not initiated by traces of perruthenate present as a contaminant in the ruthenate solutions. This conclusion is supported by both the kinetic rate law for the reaction and the products obtained from the oxidation of alcohols that would be expected to react differently with [Formula: see text] and [Formula: see text].

We have investigated the mechanism for the aminolysis of p-nitrophenyl iV-phenylcarbamate (la) in toluene.2 As will be shown below, la reacts in the nonpolar solvent