Novel tocopheryl compounds. Part 16: Nitration of α-tocopheryl acetate—a mechanistic study

The reaction of α-tocopheryl acetate (vitamin E acetate, ) with concentrated nitric acid proceeds according to a non-radical, two-step mechanism, producing 5-nitromethyl-γ-tocopheryl acetate () in good yields. In the first step, oxidation of affords a benzylic cation intermediate (), which in the second step adds nitrite to give . The acetyl group, which stabilizes intermediate intramolecularly, remains bound to the tocopheryl moiety throughout the reaction.