Phenylethynylpentafluorobenzene and phenylethynylpentachlorobenzene

Rausch, Marvin D.; Siegel, Armand; Kelmann, L. P.

doi:10.1021/jo01254a050

Cited by 13 publications

(7 citation statements)

References 1 publication

(1 reference statement)

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“…MS (CI/NH 3 ), negative ion): m / z (ion, relative intensity) 804.4 (M, 61.86). Its mass spectrum compared favorably with literature values . No 1 H, 13 C, or 19 F NMR spectral data were found in the literature.…”

Section: Methodsmentioning

confidence: 47%

“…Si 2 F 6 was synthesized from SbF 3 and Si 2 Cl 6 according to a literature method . Phenyl pentafluorophenylacetylene was synthesized from iodopentafluorobenzene and copper phenylacetylenide and was purified by sublimation. 1 H and 13 C NMR spectra were recorded on a Varian VXR-300 instrument and mass spectra were obtained on a Finnigan 4000 (70 eV EI or CI).…”

Section: Methodsmentioning

confidence: 99%

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Disilane-Catalyzed and Thermally Induced Oligomerizations of Alkynes: A Comparison

and

Verkade

2000

Organometallics

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The alkynes RCtCR (R ) H, Et, Ph), RCtCH (R ) Me(CH 2 ) 5 , Me(CH 2 ) 7 , Ph, Me 3 Si, EtO 2 C), and RCtCR′ (R ) Ph, R′ ) C 6 F 5 ; R ) Me, R′ ) Ph) trimerize to corresponding benzene derivatives in 30-100% yields in the presence of Si 2 Cl 6 as a procatalyst at 170-200 °C over 20-48 h. These reactions represent only the second example of nonmetal-catalyzed alkyne trimerizations. The unsymmetrical alkynes Me 3 SiCtCH, EtO 2 CCtCH, and PhCtCC 6 F 5 gave symmetrical 1,3,5-substituted benzenes, while the others led to isomeric mixtures. A 1:2 molar mixture of PhCtCH and PhCtCPh provided an isomeric mixture (45% yield) consisting mainly of 1,2,4,5-tetraphenylbenzene. While Si 2 (OMe) 6 also catalyzed alkyne trimerizations (though not as efficiently as Si 2 Cl 6 ), Si 2 Me 6 did not, suggesting an electronegativity influence in the formation of the Cl 3 Si • radicals shown to be involved in these reactions. Somewhat unexpectedly, however, neither Si 2 F 6 nor sym-Si 2 Me 2 Cl 4 catalyzed alkyne trimerizations. Experimental support for the radical pathway proposed for the alkyne trimerization observed herein is presented. In the absence of disilane procatalyst, PhCtCH gave an isomeric mixture of dimers, p-MeC 6 H 4 CtCH afforded predominantly a single dimer, and 1-ethynyl-1-cyclohexene provided exclusively a single dimer, whereas RCtCH (R ) alkyl) and PhCtCMe did not react upon heating under the same conditions.

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Section: Methodsmentioning

confidence: 47%

Section: Methodsmentioning

confidence: 99%

Disilane-Catalyzed and Thermally Induced Oligomerizations of Alkynes: A Comparison

and

Verkade

2000

Organometallics

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“…General Remarks: 9,9-Dimethyl-2,7-diiodofluorene (1), [50] Fc-CϵCH (3), [78] and Rc-CϵCH (5) [79] were prepared following published procedures. All other chemicals are commercially available and were used as received.…”

Section: Chemical Synthesismentioning

confidence: 99%

Synthesis, Electrochemical Behavior, and Self‐Assembly of Metallocene‐Functionalized Thiofluorenes

et al. 2010

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Keywords: Metallocenes / Thiols / Fused ring systems / Self-assembly / Monolayers / Cyclic voltammetry With a view to preparing organometallics for the fabrication of self-assembled monolayers (SAMs) and their possible electrochemical applications, we report the synthesis and characterization of ferrocene-and ruthenocene-functionalized thiofluorenes 4b and 6b, respectively. These sandwich compounds were accessible through a consecutive synthesis methodology. 9,9-Dimethyl-2,7-diiodofluorene (1) with tBuLi, S 8 , and Me(CO)Cl gave 9,9-dimethyl-2-iodo-7-thioacetylfluorene (2)

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“…B.6, Riedel de Haen) was used for filtrations. Hdpf, [19] [(tmeda)ZnCl 2 ], [23] [(pmdta)ZnCl 2 ], [24] [Ti](Me) 2 , [25] [Ti]Cl 2 , [26] HCϵCFc, [27] HCϵCRc, [28] and [(tht)AuCl] [29] were prepared according to published procedures. Infrared spectra were recorded with a PerkinElmer FT-IR spectrometer Spectrum 1000.…”

Section: Methodsmentioning

confidence: 99%

Heterometallic Transition‐Metal Complexes Based on 1‐Carboxy‐1′‐(diphenylphosphanyl)ferrocene, (tmeda/pmdta)Zinc(II), and Gold(I) Units

2008

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Phenylethynylpentafluorobenzene and phenylethynylpentachlorobenzene

Cited by 13 publications

References 1 publication

Disilane-Catalyzed and Thermally Induced Oligomerizations of Alkynes: A Comparison

Disilane-Catalyzed and Thermally Induced Oligomerizations of Alkynes: A Comparison

Synthesis, Electrochemical Behavior, and Self‐Assembly of Metallocene‐Functionalized Thiofluorenes

Heterometallic Transition‐Metal Complexes Based on 1‐Carboxy‐1′‐(diphenylphosphanyl)ferrocene, (tmeda/pmdta)Zinc(II), and Gold(I) Units

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