Abstract

The electrolysis of 1-acetylnaphthalene at a controlled potential [DMF, Ba· (CIO4)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 60%); 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 presence of lithium cations.

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