Oxofunctionalized Trans-2-carboxycinnamic Acids by Catalytic Domino Oxidation of Naphthols and Hydronaphthoquinones |
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| Authors: | Mirosław Giurg Hubert Muchalski Ewa Kowal |
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| Institution: | 1. Faculty of Chemistry , Department of Organic Chemistry, Wroc?aw University of Technology , Wroc?aw , Poland miroslaw.giurg@pwr.wroc.pl;3. Faculty of Chemistry , Department of Organic Chemistry, Wroc?aw University of Technology , Wroc?aw , Poland |
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| Abstract: | The catalytic oxidation of naphthalenes was investigated. Hydrogen peroxide (30% aqueous) was used as an oxygen source, and 2,2’-dinitro-4,4’-ditrifluoromethyldiphenyl diselenide was the oxygen-transfer catalyst. Unsubstituted naphthols produce trans-2-carboxycinnamic acid in nearly quantitative yields. Both naphthols bearing substituents on the conjugated ring deliver corresponding trans-2-carboxycinnamic acids in good to excellent yields. The 1,7- and 2,6-hydronaphthoquinones, substituted by carboxy and carboxymethyl groups, produce hydroxycinnamic acids in satisfactory to excellent yields. A catalytic domino reaction mechanism is proposed. |
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| Keywords: | Catalysis cinnamic acids domino reaction naphthalenes oxidation selenium |
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