Are allylic three degree alcohols oxidized by the Jones' reagent via a classical carbocation intermediate?
It makes sense. Jones's oxidation occurs in presence of a strong acid. Hence, the oxygen can get protonated and leave as a water molecule, giving rise to a tertiary carbocation. The charge can then delocalize, the secondary alcohol get formed, and this alcohol then undergo oxidation. The oxidation will probably drive the equilibrium towards the product.