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

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• 作者：Nguyen Huu Dinh ; Trinh Thi Huan ; Duong Ngoc Toan ; Peter Mangwala Kimpende ; Luc Van Meervelt
• 关键词：Tautomer ; Nitro-aci tautomerization ; Nitrophenol ; Eugenoxyacetic acid ; Quinone
• 刊名：Journal of Molecular Structure
• 出版年：2010
• 出版时间：10 September 2010
• 年：2010
• 卷：980
• 期：1-3
• 页码：137-142
• 全文大小：530 K

文摘

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.