An Efficient Synthesis of 1,3-Dialkylimidazole-2-Selenones

Tian, Fang; Chen, Yahong; Wu, Lan; Li, Peng; Lü, Shiwei

doi:10.3184/174751914x14007821182269

Cited by 5 publications

(4 citation statements)

References 16 publications

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“…When the imidazolium salt 9 was reacted with two equivalents of the strong base KO t Bu, both Me 3 Si‐vinyl bonds were cleaved and the parent imidazole‐2‐selone 12 was quantitatively formed upon subsequent addition of black selenium to the reaction solution. Compound 12 has previously been prepared in a related procedure by reacting 1,3‐dimethylimidazolium chloride with selenium in the presence of bases [25] . The analytical data obtained for our product are consistent with the values reported there.…”

Section: Resultssupporting

confidence: 86%

“…Compound 12 has previously been prepared in a related procedure by reacting 1,3-dimethylimidazolium chloride with selenium in the presence of bases. [25] The analytical data obtained for our product are consistent with the values reported there. The cleavage of both Si-vinyl bonds in our product is clearly indicated by the disappearance of the typical SiMe 3 lines at δ 1 H = 0-0.5 ppm and δ 13 C = 0-10 ppm and by the appearance of new signals characteristic of the HÀ C=CÀ H moiety at δ 1 H = 6.83 ppm and δ 13 C = 119.7 ppm.…”

Section: Reactivity Studiessupporting

confidence: 90%

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Synthesis and Properties of Backbone Silylated Imidazol‐2‐thiones

et al. 2023

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Imidazole‐2‐thiones have attracted considerable interest in the past as materials for potential applications in the pharmaceutical and chemical industries. Herein, the synthesis of a series of backbone silylated 1,3‐dialkylimidazol‐2‐thiones is reported. The developed synthesis protocol involves the silylation of N,N‐dimethylimidazol‐2‐thione 1 followed by the addition of organochlorosilanes RnSiCl4–n (R=Me, Ph; n=0–4) and enabled the synthesis of the C‐silylated derivatives with monocyclic, silyl‐bridged or fused tricyclic structures. Reactivity studies performed with N,N‐dimethyl‐4,5‐bistrimethylsilylimidazole‐2‐thione as a model substance showed surprisingly stable silicon‐vinyl bonds and reactivity patterns closely related to those observed for the unsilylated species 1. Combined UV‐spectroscopic and computational studies revealed only minor impact of the silyl substituents on the electronic structure of the imidazol‐2‐thione ring.

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Section: Resultssupporting

confidence: 86%

Section: Reactivity Studiessupporting

confidence: 90%

Synthesis and Properties of Backbone Silylated Imidazol‐2‐thiones

et al. 2023

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“…Our previous studies found that HSe – had a strong reductive ability and could reduce SO 2 easily . In this study, inspired by the selenium-catalyzed reduction of organic compounds using CO, − we suggest a new strategy to reduce SO 2 by CO using selenium as the catalyst in the liquid phase. A common polar aprotic and nonvolatile solvent DMF and H 2 O mixture solution was used as the solvent.…”

Section: Introductionmentioning

confidence: 90%

Selenium-Assisted Reduction of Sulfur Dioxide by Carbon Monoxide in the Liquid Phase

Yang

Chai

Zhu

et al. 2017

Ind. Eng. Chem. Res.

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Regenerable flue gas desulfurization (FGD) is highly attractive because of the transformation of sulfur dioxide (SO2) to high-value products. In this study, selenium-assisted SO2 reduction by carbon monoxide (CO) in the liquid phase [dimethylformamide (DMF) + water (H2O) mixture] is proposed and applied in the FGD process. This process realizes recycle of the elemental sulfur product under room temperature. Moreover, results show that both the selenium catalyst and DMF solvent have good stability and can be well recycled, implying that this process is economically feasible. Furthermore, the mechanism of selenium-assisted SO2 reduction by CO in DMF/H2O is investigated. Results show that the selenium catalyst dissolves in solution and forms Se n 2– species, which are the active intermediates and promote formation of the sulfur product.

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“…Recently, we also have reported the synthesis of 1,3-dialkylimidazole-2-selenones using 1,3-dialkylimidazolium salts with selenium in water or in ethanol or acetone [16,17]. Keeping this result in mind, we reported 1,3-dialkylimidazole-2-selenone catalyzed oxidative carbonylation of aromatic amines with carbon monoxide in the presence of oxygen in ionic liquids (Scheme 1).…”

Section: Introductionmentioning

confidence: 90%