Perfluoro(alkylsilanes). II. Trifluoro(trifluoromethyl)silane and trifluoro(pentafluoroethyl)silane

Sharp, Kenneth G.; Coyle, T. D.

doi:10.1021/ic50112a021

Cited by 41 publications

(30 citation statements)

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“…(1), (2)]. [4] Despite the knowledge of this fact for about 40 years, only a few pentafluoroethyl silanes have been synthesized. Moreover, based on Sharps and Coyles observations, the existence of silanes with more than two pentafluoroethyl substituents at ambient temperature is very conceivable.…”

mentioning

confidence: 99%

“…Reaction of SiCl 4 [6] The course of this transformation involves the initial formation of (C 2 F 5 ) 3 SiCl from SiCl 4 and three equivalents of LiC 2 F 5 (Scheme 1). The next two equivalents of LiC 2 F 5 serve as fluoride sources, which convert the Lewis acidic (C 2 F 5 ) 3 SiCl into the tris(pentafluoroethyl)difluorosilicate ion.…”

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confidence: 99%

“…More generally, this compound is the first structurally characterized example of a tris(perfluoroalkyl)silicon compound. [12] We succeeded in the preparation and full characterization of [ 4 and LiC 2 F 5 as starting materials, and a mechanism for the multistep generation of these silicates was presented. Future studies in our laboratory are focused on neutral tris(pentafluoroethyl)silanes and the most challenging silane Si(C 2 F 5 ) 4 .…”

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confidence: 99%

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Synthesis of Five‐ and Six‐Coordinate Tris(pentafluoroethyl)fluorosilicates

Steinhauer¹,

Stammler²,

Neumann³

et al. 2013

Angew Chem Int Ed

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The research area of perfluoroalkylsilanes is still in its infancy. Although there are already many examples of difluorotriorganylsilicates, the first example of a completely characterized trifluorotriorganylsilicate is presented, the dianion [Si(C2 F5 )3 F3 ](2-) . The strongly electron-withdrawing influence of the pentafluoroethyl groups appears to be a fundamental cause of the stability of this compound. This dianion is also the first structurally characterized example of a tris(pentafluoroethyl)silicon compound. The synthesis and complete characterization of [PPh4 ]2 [Si(C2 F5 )3 F3 ] and [PPh4 ][Si(C2 F5 )3 F2 ] along with the precursor [H(OEt2 )2 ][Si(C2 F5 )3 F2 ] was achieved from SiCl4 and LiC2 F5 .

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Synthesis of Five‐ and Six‐Coordinate Tris(pentafluoroethyl)fluorosilicates

Steinhauer¹,

Stammler²,

Neumann³

et al. 2013

Angew Chem Int Ed

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“…Über-einstimmend damit konnten (CF 3 ) 3 SiCl und (CF 3 ) 3 SiNEt 2 spektroskopisch nachgewiesen, jedoch bislang nicht isoliert werden. [2] Trotz anderslautender Behauptungen aus der Literatur [3] gibt es keinerlei Hinweise auf die Existenz von Si(CF 3 ) 4 .…”

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Penta‐ und hexakoordinierte Tris(pentafluorethyl)fluorosilicate

et al. 2013

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“…Additionally, in the absence of carbene trapping reagents, the CFCF 3 affords perfluoro-2-butenes by carbene dimerization. 32,33 However, in Yang's experiments, no tetrafluoroethene, perfluoro-2-butenes, or relevant captured products were detected. 10 These can be interpreted as due to the strong combination of CFCF 3 and graphite(001) surface, which is analogous to CF 2 .…”

Section: Resultsmentioning

confidence: 94%

CF₃I Synthesis Catalyzed by Activated Carbon: A Density Functional Theory Study

TaiPing²,

Liu

et al. 2014

J. Phys. Chem. A

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A revised reaction mechanism of CF3I synthesis catalyzed by activated carbon is investigated with quantum chemistry methods using density functional theory (DFT). The adsorption configurations of possible intermediates are carefully examined. The reaction pathway and related transition states are also analyzed. According to our calculations, first, the dehydrofluorination of CHF3 is catalyzed by -COOH groups, which possesses the highest barrier and is accordingly identified as the rate-determining step. Second, the difluorocarbene disproportionation over graphite (001) surface proceeds instead of dimerization. The next reaction steps involving the association of fluoromethine and trifluoromethyl, the fluorine abstractions between intermediates and the iodine abstractions by the desorbed CF3 and CF2CF3 from molecular iodine are also feasible over graphite (001) surfaces. It is also found that the coke deposition in experiments is due to the fluorine abstraction from fluoromethine. This revised mechanism is in agreement with available experimental data and our theoretical computations.

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Perfluoro(alkylsilanes). II. Trifluoro(trifluoromethyl)silane and trifluoro(pentafluoroethyl)silane

Cited by 41 publications

References 1 publication

Synthesis of Five‐ and Six‐Coordinate Tris(pentafluoroethyl)fluorosilicates

Synthesis of Five‐ and Six‐Coordinate Tris(pentafluoroethyl)fluorosilicates

Penta‐ und hexakoordinierte Tris(pentafluorethyl)fluorosilicate

CF₃I Synthesis Catalyzed by Activated Carbon: A Density Functional Theory Study

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Perfluoro(alkylsilanes). II. Trifluoro(trifluoromethyl)silane and trifluoro(pentafluoroethyl)silane

Cited by 41 publications

References 1 publication

Synthesis of Five‐ and Six‐Coordinate Tris(pentafluoroethyl)fluorosilicates

Synthesis of Five‐ and Six‐Coordinate Tris(pentafluoroethyl)fluorosilicates

Penta‐ und hexakoordinierte Tris(pentafluorethyl)fluorosilicate

CF3I Synthesis Catalyzed by Activated Carbon: A Density Functional Theory Study

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CF₃I Synthesis Catalyzed by Activated Carbon: A Density Functional Theory Study