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

被引：21
|
作者：
Karpov, Sergey V. [1 ]
Grigor'ev, Arthur A. [1 ]
Kayukov, Yakov S. [1 ]
Karpova, Irina V. [1 ]
Nasakin, Oleg E. [1 ]
Tafeenko, Victor A. [2 ]
机构：
[1] IN Ulyanov Chuvash State Univ, Moskovskii Prospekt 15, Cheboksary 428015, Russia
[2] Lomonosov Moscow State Univ, Leninskiye Gory 1-3, Moscow 119991, Russia
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 15期
关键词：
MAGNETIC-PROPERTIES; 2,2,3,3-TETRACYANOCYCLOPROPYL KETONES; CRYSTAL-STRUCTURES; HYDROGEN HALIDES; SPIN-CROSSOVER; LIGAND; HETEROCYCLIZATION; CYANOCARBANION; COMPLEXES; CHEMISTRY;
D O I：
10.1021/acs.joc.6b01040
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 alpha-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.
引用
收藏
页码：6402 / 6408
页数：7
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