Synthesis, spectral and electrochemical characterization of novel 2-(fluoroanilino)-1,4-naphthoquinones

• Published in: Journal of fluorine chemistry Vol. 132; no. 2; pp. 94 - 101
• Main Authors: Leyva, Elisa, López, Lluvia I., Loredo-Carrillo, Silvia E., Rodríguez-Kessler, Margarita, Montes-Rojas, Antonio
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-02-2011
• Subjects: 2-(Fluoroanilino)-1,4-naphthoquinone; CeCl 3·7H 2O; Derivatives; Electrochemical oxidation; Electronic properties; Fluorine; Lewis acid; Lewis acid catalyst; Microwave; Microwaves; Spectra; Synthesis (chemistry); Voltammetry; Microwave; CeCl 3·7H 2O; 2-(Fluoroanilino)-1,4-naphthoquinone; Lewis acid catalyst; Electrochemical oxidation
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2010.12.001

Novel 2-(fluoroanilino)-1,4-naphthoquinones were prepared reacting the corresponding fluoroaniline and 1,4-naphthoquinone in the presence of a Lewis acid catalyst with strong oxidation properties such as CeCl
3·7H
2O. This preparation was also investigated under microwave irradiation. All 1,4-naphthoquinone derivatives were characterized by UV–Vis, IR,
1H and
19F NMR, MS and cyclic voltammetry.
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▶ Synthesis and characterization of 2-(fluoroanilino)-1,4-naphthoquinone. ▶ Synthesis of naphthoquinone derivatives with Lewis catalysts and oxidizing agents. ▶ The synthesis was also carried out under microwave irradiation. ▶ Compounds were characterized by UV–Vis,
1H and
19F NMR, M.S. and electrochemistry.
The preparation of novel 2-(fluoroanilino)-1,4-naphthoquinones is presented. It takes place under mild conditions by reacting the corresponding fluoroaniline and 1,4-naphthoquinone in the presence of a Lewis acid catalyst with strong oxidation properties such as CeCl
3·7H
2O. This preparation was also investigated under microwave irradiation. All 1,4-naphthoquinone derivatives were characterized by UV–Vis, IR,
1H and
19F NMR, MS and cyclic voltammetry, to investigate the effect of the fluoro-substituents on their electronic properties.