Alkoxymercuration-demercuration is a formal addition reaction in organic chemistry that converts alkenes into ethers via anti-addition across the double bond, adhering to Markovnikov regioselectivity where the alkoxyl group attaches to the most substituted carbon. The mechanism proceeds through a cyclic mercurinium ion intermediate stabilized by resonance, which directs nucleophilic attack while suppressing carbocation rearrangements inherent in acid-catalyzed hydration pathways. This transformation utilizes mercury(II) acetate as an electrophile and sodium borohydride for reductive demercuration to establish the final stereochemical and structural outcome within synthetic organic methodology.
Alkoxymercuration-demercuration is a formal addition reaction in organic chemistry that converts alkenes into ethers via anti-addition across the double bond, adhering to Markovnikov regioselectivity…