The hydroxylation of alkanes and alkyl chains

A solution of 30% aqueous H₂O₂ in trifluoroacetic acid converts linear alkanes and cycloalkanes to an equilibrium mixture of secondary alcohols and their trifluoroacetates. There is no trace of further oxidation to ketones. Yields and conversions can be 70–90%, but are limited by elimination and epoxidation to form vicinal glycols. Linear alkyl chains are also hydroxylated in good yields with selectivity for introducing the alcohol group remote from electronegative substituents. The active reagent is trifluoroperoxyacetic acid, and it is effective in the presence of 4–10% water. When tertiary hydrogens are present, the oxidations are more complex.