Peroxy formic hydroxylation

The standard procedure for the vicinal hydroxylation of oleic acid in the laboratory is the use of peroxy formic acid in situ with subsequent alkaline hydrolysis of the hy-... 

The absence of methyl hydroperoxide in the results of Hanst and Calvert38 cannot be considered conclusive and it is very likely that methyl radicals will be oxidized to methyl hydroperoxide, in this system as in other systems (e.g., CH3I photooxidation), where a readily available hydrogen atom is present. Decomposition to give methanol and/or formaldehyde might quickly follow and Hanst and Calvert say that under their conditions formaldehyde would quickly be converted to formic acid. The chain ending steps that they postulate [(96) and (21)] are quite possible, but if one accepts the reaction between hydroxyl radicals and methyl peroxy radicals as put forward for CHSI photooxidation,10 one might equally accept a similar reaction... 

Organic peroxy acids are well-known reagents for aromatic hydroxylation of arenes [42, 43]. m-Chloroperbenzoic acid was applied to prepare quinones in low to moderate yields [54]. Peroxy acids can be generated in situ from and carboxylic acids or via aldehyde autoxidation [42]. Arnold et al. reported the synthesis of menadione in ca. 30% yield by using 30% in acetic acid [55]. Following this strategy, Orita et al. oxidized a range of arenes by an excess of in formic... 

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