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Isolation, structure, and properties of quinone-aci tautomer of a phenol-nitro compound related to eugenoxyacetic acid

Treatment with excess nitric acid in acetic acid revealed that eugenoxyacetic acid underwent an unexpected ether cleavage, a normal nitration, and then an unexpected electrophilic addition to the double bond of the side chain that led to the formation of a dinitro compound which subsequently converted to a sensitive, reactive quinone-aci compound. The structure of the quinone-aci compound (1) and its derivatives (2-6) was established by 1D- , 2D NMR, MS spectra, and chemical methods. In addition, the XRD structure of compound 2 derived from 1 was established. A double tautomerization of 1 in solution was studied by the LC-UV-MS method. © 2010 Elsevier B.V. All rights reserved.

 Dinh N.H., Huan T.T., Toan D.N., Kimpende P.M., Meervelt L.V.
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  Từ khóa : Eugenoxyacetic acid; Nitrophenols; Quinone; Tautomer; Tautomerizations; Chemical bonds; Ethers; Nitric acid; Phenols; Acids