Vinylogy the α-carbon immediately adjacent to the carbonyl, as would a simple enolate. Allylic electrophiles often react by vinylogous attack of a nucleophile rather than direct addition. A further example of vinylogous reactivity: ascorbic acid (Vitamin C) behaves as a vinylogous carboxylic acid by involvement of its carbonyl moiety, a vinyl group within the ring, and the lone pair on the hydroxyl group acting as the conjugated system. Acidity of the hydroxyl proton at the terminus of the vinyl group in ascorbic acid is more comparable to a typical carboxylic acid than an alcohol because two major resonance structures stabilize the
Vitamin C efficiency decreases as amounts increase. Intravenous administration bypasses this. Doing so makes it possible to achieve plasma concentrations of 5 to 10 millimoles/liter (mmol/L), which far exceed the approximately 0.2 mmol/L limit from oral consumption. The theories of mechanism are contradictory. At high tissue concentrations ascorbic acid is described as acting as a pro-oxidant, generating hydrogen peroxide (HO) to kill tumor cells. The same literature claims that ascorbic acid acts as an antioxidant, thereby reducing the adverse effects of chemotherapy and radiation therapy. Research continues in this field, but a 2014 review concluded: "Currently, the use of high-dose intravenous vitamin