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.
KeywordsAlkylnaphthalenes; Cyclic voltammetry; Electro-oxidation; Binaphthyls; AM1 method.
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- Schmittel, M, Burghart, A 1997Angew Chem Int Ed Engl362551Google Scholar
- Smith, JRL, Shaw, BAJ, Foulkes, DM, Jeffrey, AM, Jerina, DM 1977J Chem Soc Perkin Trans21583Google Scholar
- Soanna, F, Sturini, M, Cermenati, L, Albini, A 2000J Chem Soc Perkin Trans2699Google Scholar
- Boyland E, Sims P (1953) J Chem Soc:2966Google Scholar
- Sydnes, LK, Burkov, IC, Hansen, SH 1985Tetrahedron415706Google Scholar
- Eberson, L, Hartshorn, MP, Persson, O 1995J Chem Soc Perkin Trans2409Google Scholar
- Eberson L, Hartshorn MP, Persson O, Robinson WT, Timmerman-Vaughan DJ (1995) Acta Chem Scand:49Google Scholar
- March, J 1992Advanced Organic Chemistry4John WileyNew York539Google Scholar
- Millauer H (1995) Ger Pat DE 4342282Google Scholar
- Stewart, JJP 1998WinMOPAC 2.0, User ManualFujitsu LimitedTokyo, JapanGoogle Scholar
- Spiegel, MR 1968Mathematical HandbookMcGraw-HillNew York47Google Scholar
- Gilchrist, TL, Storr, RC 1972Organic reactions and orbital symmetryCambidge University PressCambridgeGoogle Scholar
- Sioda, RE, Frankowska, B, Łobuzińska, A, Fahidy, TZ 2004Pol J Chem781567Google Scholar