Synthesis and X-ray Characterization of Alkali Metal 2-Acyl-1,1,3,3-tetracyanopropenides

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• 作者：Sergey V. Karpov ; Arthur A. Grigor’ev ; Yakov S. Kayukov ; Irina V. Karpova ; Oleg E. Nasakin ; Victor A. Tafeenko
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：81
• 期：15
• 页码：6402-6408
• 全文大小：374K
• 年卷期：0
• ISSN：1520-6904

文摘

A novel route for synthesis of 2-acyl-1,1,3,3-tetracyanopropenides (ATCN) salts in high yields and excellent purities starting from readily available methyl ketones, malononitrile, bromine, and alkali metal acetates is reported. The starting aryl(heteroaryl) methyl ketones were oxidized to the corresponding α-ketoaldehydes by new a DMSO–NaBr–H₂SO₄ oxidation system in yields up to 90% within a short reaction time of 8–10 min. The subsequent stages of ATCN preparation are realized in aqueous media without use of any toxic solvents, in accordance with principle 5 of “green chemistry”. Lithium, sodium, potassium, rubidium, and cesium 2-benzoyl-1,1,3,3-tetracyanopropenides were characterized by X-ray diffraction analysis. These salts show a good potential for synthesis of five- and six-membered heterocycles and may serve as potentially useful ligands in coordination and supramolecular chemistry.