Electrochemical oxidative dehydrodimerization of naphthylamines. An efficient synthesis of 8,8-dianilino-5,5'-binaphthalene-1,1'-disulfonate

Abstract

mA (current density: 1.6 A/dm2). After 8.0 F/mol of electricity was passed, the reaction mixture was poured into 100 mL of a saturated sodium chloride solution and extracted with three 50-mL portions of ether. The combined ethereal solution was dried over anhydrous magnesium sulfate, filtered, and concentrated to give an oily material, which was then fractionally distilled to form almost pure 2-methyl-4-methoxyphenol (8) in 42% yield; mp 71-72 °C [lit.28 mp 71-72 °C].

Iron-Catalyzed Synthesis, Structure, and Photophysical Properties of Tetraarylnaphthidines

“…The 1 H-NMR, 13 C-NMR, and DEPT spectra of compound 4 displayed signals for a highly symmetrical compound. Signals for nine aromatic CH and five quaternary aromatic carbon atoms were identified.…”

“…The third system is formed by H-10, H-11, H-12, and H-13. The assignment of all 13 C-NMR signals to the respective 1 H-NMR signals could be achieved by an HSQC measurement ( Figure 2 and Table S1). The constitution of naphthidine 4 was confirmed by analysis of the HMBC spectrum (Supplementary Material, HMBC of compound 4, Table S1) The structural assignment for N,N,N',N'-tetraphenylnaphthidine (4) was confirmed by an X-ray crystal structure determination ( Figure 3).…”

“…Naphthidines (1,1′-binaphthalene-4,4′-diamines) have also been studied because of their ready oxidation to radical cations [9][10][11][12]. Starting from the corresponding 1-naphthylamines by an oxidative coupling, the synthesis of naphthidines can be induced electrochemically [9,10,13], by stoichiometric amounts of titanium tetrachloride [11], stoichiometric amounts of iron(III) chloride [14], chloranil [15], or (bis(trifluoroacetoxy)iodo)benzene (PIFA) [16]. It has been well-known for a long time that naphthidines can be separated into their stable atropisomers [17].…”

“…The following data are available online. Copies of the 1 H-NMR,13 C-NMR, DEPT (θ = 135 • ), UV, and fluorescence spectra of the compounds 3, 4, and 5; copies of the 2D-NMR spectra (COSY, HSQC, HMBC, NOESY, 1 H/ 15 N-HMBC, JRES) of the compounds 4 and 5. Author Contributions: A.P.…”

A protocol for the combined sub-fractionation and delipidation of lipid binding proteins using hydrophobic interaction chromatography

“…bisANS was synthesized according to a modified literature procedure [25] described in detail in the supplementary information. …”