Permanganate–periodate oxidation. Part VIII. The oxidation of some cyclic mono-olefins and monoterpenes

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Abstract
The reaction of cyclic mono-olefins with the permanganate–periodate reagent was investigated. 4-Terpinenol and its acetate, and to a lesser degree α-terpineol and camphene gave in addition to the expected products, several neutral and acidic products. In contrast, α-pinene, β-pinene, sabinene, pulegone, and several cyclo-olefins which can be considered as simple analogues of these monoterpenes, afforded the predicted products in high yield. Cyclo-hexanone and menthone, though saturated, were oxidized extensively, enolization offering a plausible pathway for this result. Saturated terpene alcohols reacted only very slowly indicating that attack at a tertiary hydrogen is not a significant part of the permanganate–periodate reaction.

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