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6

The selective Baeyer-Villiger Oxidation of unsaturated ketones is definitely depends on the conditions used. I do not want to eloborate this fact any further because it was well documented in Waylander's answer. Howevr, so far into the literature suggest that use of peracids in presence of unsaturation in the substrate ketone is not a good idea. The quote "...


8

The answer appears to be "it depends" (perhaps this should not surprise an experienced organic chemist). According to the abstract of the paper by Mendelovici and Glotter [1] in steroid chemistry: Treatment of 3β- and 3α-hydroxy-(acetoxy-)cholest-4-en-6-one and of 6β-and 6α-hydroxy-(acetoxy-)cholest-4-en-3-one with MCPBA gives two types of product, ...


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