, Volume 139, Issue 5, pp 513-519
Date: 21 Mar 2008

Electro-oxidation of certain naphthalene derivatives

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Naphthalene and alkylnaphthalenes are electro-oxidized to give many products, of which 1,4-naphthoquinones and binaphthyls are the most stable, especially in the case of substrates, which are not substituted in α-positions. On the other hand, α-substituted naphthalenes give the respective naphthoquinols as the main products. Interestingly, 1,2-naphthoquinones are not separated as products, instead, a fragmentation of one of the rings leads to oxidation products, in which the 1,2-bond in naphthalene is broken to form dialdehydes or diketones. An anodic formation of binaphthyls is described, starting from alkyl-substituted naphthalenes, dissolved in acetone-water (1:1 v/v) and using 0.1 M (CH3)4N(BF4) supporting electrolyte. Several isomeric binaphthyls were obtained depending on the substrates. The structure of the binaphthyls formed is discussed based on molecular orbital calculations using the AM1 program. Cyclic voltammetric oxidation curves are shown for naphthalene and three methyl derivatives.