INFLUENCE OF THE NATURE OF THE BASE ELECTROLYTE ON THE REGIOSELECTIVITY OF THE CATHODIC HYDRODIMERIZATION OF 1-ACETYLNAPHTHALENE IN AN APROTIC MEDIUM

Article abstract of DOI:10.1007/BF00965434

The electrolysis of 1-acetylnaphthalene at a controlled potential (DMF, Ba(ClO4)2) leads to the formation of 5-acetyl-1,2,4,5-tetrahydro-2-methyl-2-(1-naphthyl)-1,4-methano-3-benzoxepine (yield of 60percent); this is explained by the stabilization of the dimeric dianion of the "Head-tail" type by the Ba²⁺ cations.The formation of 2,3-dimethyl-2,3-di-(1-naphthyl)-butane-2,3-diol is observed with the acylotropic rearrangement of the intermediate anion, leading to 2-acetylnaphthalene, in the presenc of lithium cations.