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 convert...

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Bibliographic Details
Published in:Journal of molecular structure 2010-09, Vol.980 (1), p.137-142
Main Authors: Dinh, Nguyen Huu, Huan, Trinh Thi, Toan, Duong Ngoc, Kimpende, Peter Mangwala, Meervelt, Luc Van
Format: Article
Language:English
Subjects:
Bonding
Eugenoxyacetic acid
Nitro-aci tautomerization
Nitrophenol
Quinone
Tautomer
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Summary: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.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2010.07.005