Syntheses and Structures of Silyl-Group-Containing Hexaalkylated Benzenes

Cho, Eun Jeong; Lee, Vladimir; Yoo, Bok Ryul; Jung, Il Nam; Sohn, Honglae; Powell, Douglas R.; West, Robert

doi:10.1021/om970393j

Cited by 17 publications

(6 citation statements)

References 27 publications

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“…This leads to flexible ethyl functions with Lewis acidic centres in the target molecule. Until now, trimethylsilyl‐functionalised benzenes were not synthesised by hydrosilylation based on trivinylbenzene but by Friedel–Crafts alkylation of benzene with vinyldichloromethylsilane . However, the product in this process is only a by‐product of the polyalkylation of benzene with dichloromethylvinylsilane and has not been specifically synthesised and isolated.…”

Section: Introductionmentioning

confidence: 99%

Tridentate Lewis Acids: Silicon‐Functionalised 1,3,5‐Triethynylbenzene and 1,3,5‐Trivinylbenzene

et al. 2018

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Planar tridentate Lewis acids were synthesised by hydrosilylation reactions of triethynylbenzene with chlorosilanes. Hydrogenation of the rigid triethynylbenzene using hydrogen in the presence of Lindlar's catalyst resulted in the formation of trivinylbenzene. The hydrosilylation of this compound enabled the synthesis of flexible tridentate Lewis acids with SiClMe 2 and SiCl 2 Me, SiCl 3 groups. In order to increase the acidity, the [a] 2533 Scheme 2. Synthesis of 1,3,5-tris[(trimethylsilyl)ethynyl]benzene by Sonogashira cross-coupling reaction of 1,3,5-tribromobenzene and subsequent deprotection to 1,3,5-triethynylbenzene. Reagents and conditions: i) 1. TMSacetylene, I Pr 2 NH, CuI, PdCl 2 (PPh 3 ) 2 , reflux, 1 d; 2. aq. workup, 91 %; ii) THF, EtOH, 1 M NaOH, room temp., 1 d, 80 %.Scheme 3. Lindlar reduction of 1,3,5-trithynylbenzene and determination of conversion using GC-MS analysis after 18 h reaction time. Reagents and conditions: i) 1. EtOAc, Lindlar catalyst, quinoline, H 2 , room temp., 18 h; 2. aq. workup, 62 %.The gas chromatogram shows the presence of three other compounds resulting from further reduction of the double bonds in 3. Shorter reaction times, however, lead to incomplete Eur.

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Section: Introductionmentioning

confidence: 99%

Tridentate Lewis Acids: Silicon‐Functionalised 1,3,5‐Triethynylbenzene and 1,3,5‐Trivinylbenzene

et al. 2018

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“…However silicon-silicon bonds are easily oxidized 28 and a major drawback of SiNW dispersions is their thermodynamic driven tendency to lower their interfacial surface area with the environment and thus to aggregate. To prevent these issues, the hydrosilylation reaction of SiNWs could be an alternative method, 29 because the SiNWs are composed with Si-H surface. Therefore, it would be advantageous to store the SiNWs in a dry and stable state for their applications.…”

Section: Introductionmentioning

confidence: 99%

Fabrication and Characterization of Dodecyl-derivatized Silicon Nanowires for Preventing Aggregation

Shin¹,

Sohn²

2013

Bulletin of the Korean Chemical Society

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Single-crystalline silicon nanowires (SiNWs) were fabricated by using an electroless metal-assisted etching of bulk silicon wafers with silver nanoparticles obtained by wet electroless deposition. The etching of SiNWs is based on sequential treatment in aqueous solutions of silver nitrate followed by hydrofluoric acid and hydrogen peroxide. SEM observation shows that well-aligned nanowire arrays perpendicular to the surface of the Si substrate were produced. Free-standing SiNWs were then obtained using ultrasono-method in toluene. Alkylderivatized SiNWs were prepared to prevent the aggregation of SiNWs and obtained from the reaction of SiNWs and dodecene via hydrosilylation. Optical characterizations of SiNWs were achieved by FT-IR spectroscopy and indicated that the surface of SiNWs is terminated with hydrogen for fresh SiNWs and with dodecyl group for dodecyl-derivatized SiNWs, respectively. The main structures of dodecyl-derivatized SiNWs are wires and rods and their thicknesses of rods and wire are typically 150-250 and 10-20 nm, respectively. The morphology and chemical state of dodecyl-derivatized SiNWs are characterized by scanning electron microscopy, transmission electron microscopy, and X-ray photoelectron spectroscopy.

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“…Recently we reported the Friedel−Crafts alkylation of aromatic compounds with allylchlorosilanes, vinylchlorosilanes, and (chlorinated alkyl)silanes 8 to give (2-arylpropyl)-, (2-arylethyl)-, and (phenylalkyl)chlorosilanes, respectively, under mild conditions. We also studied the one-step Friedel−Crafts-type cycloalkylation of biphenyl using (dichloroalkyl)chlorosilanes, which gave in moderate yields the cyclized products, fluorenes substituted at the 9-carbon with (chlorosilyl)alkyl groups .…”

Section: Introductionmentioning

confidence: 99%

Friedel−Crafts Alkylation of Polychlorobenzenes with (1,2-Dichloroethyl)trichlorosilane

et al. 2002

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(1,2-Dichloroethyl)trichlorosilane (2) reacted with a 6-fold excess of mono-, di-, and trichlorobenzenes at 120 °C in the presence of aluminum chloride to give regiospecific (2,2-diarylethyl)trichlorosilanes via a carbocation rearrangement. The yields were 61−69%, and regioisomers of (1,2-diarylethyl)silanes were not obtained. Alkylation of 1,2,3,4-tetrachlorobenzene with 2 did not give [2,2-bis(tetrachlorophenyl)ethyl]trichlorosilane or 9,10-bis(silyl)methyl-9,10-dihydroanthracenes but gave cyclic silyl-substituted indanes in 84% yield via the acid-catalyzed dimerization of β-(trichlorosilyl)styrene formed by the first alkylation, followed by dehydrochlorination. The structure of 1,2-trans-2,3-trans-4,5,6,7-tetrachloro-1-(2,3,4,5-tetrachlorophenyl)-2-(trichlorosilyl)-3-((trichlorosilyl)methyl)indane has been determined by X-ray crystallography. The desilylated product, 1,3-cis-4,5,6,7-tetrachloro-1-(2,3,4,5-tetrachlorophenyl)-3-((trichlorosilyl)methyl)indane, was reduced by LiAlH4, and its structure was also determined.

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Syntheses and Structures of Silyl-Group-Containing Hexaalkylated Benzenes

Cited by 17 publications

References 27 publications

Tridentate Lewis Acids: Silicon‐Functionalised 1,3,5‐Triethynylbenzene and 1,3,5‐Trivinylbenzene

Tridentate Lewis Acids: Silicon‐Functionalised 1,3,5‐Triethynylbenzene and 1,3,5‐Trivinylbenzene

Fabrication and Characterization of Dodecyl-derivatized Silicon Nanowires for Preventing Aggregation

Friedel−Crafts Alkylation of Polychlorobenzenes with (1,2-Dichloroethyl)trichlorosilane

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