Vinyl Derivatives of Metals. XIII. Some Addition Reactions of Triethylperfluorovinylsilane: The F<sup>19</sup> Nuclear Resonance Spectra of the Triethylperfluorovinyl Derivatives of Silicon, Germanium, and Tin and of Perfluorovinyltriethoxysilane

Seyferth, Dietmar; Wada, Tadashi; Maciel, Gary E.

doi:10.1021/ic50002a007

Cited by 15 publications

(3 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, these systems have been little explored. Only five trifluorovinylgermane compounds have been reported, namely Ge(CFCF 2 ) 4 , , Me 2 Ge(CFCF 2 ) 2 , Me 3 GeCFCF 2 , , Et 3 GeCFCF 2 , and Ph 3 GeCFCF 2 , all in low to moderate yield, while there is a single report of a trifluorovinyllead compound, namely Pb(CFCF 2 ) 4 . There is just one report of the reactivity of such species, namely the reaction of Me 3 GeCFCF 2 with tin hydrides to yield predominantly cis -(1,2-difluorovinyl)trimethylgermane, in addition to smaller amounts of the trans and gem isomers and a range of dimeric species …”

Section: Introductionmentioning

confidence: 99%

Spectroscopic and Structural Assignment of the Absolute Stereochemistry in a Series of 1,2-Difluorovinyl Organometalloids. The First Crystallographic Characterization and Structural Series of Group 14 Fluorovinyl Compounds

et al. 2002

View full text Add to dashboard Cite

The group 14 trifluorovinyl compounds Ph(3)ECF=CF(2) (E = Ge, Sn, Pb) have been prepared in high yield by the low-temperature reaction of the triphenylelement halide with trifluorovinyllithium, generated from tetrafluoroethane (CF(3)CH(2)F, HFC-134a) and 2 equiv of n-butyllithium. The X-ray crystal structures of these materials have been obtained, so affording the first structural series for such species. Subsequent reaction of Ph(3)GeCF=CF(2) with LiAlH(4) and a range of organolithium reagents has led to preparation of the 1,2-difluorovinylgermanes Ph(3)GeCF=CFR (R = H, Me, n-Bu, t-Bu, Ph). Multinuclear NMR spectroscopic and X-ray crystallographic studies of these compounds have been undertaken and have shown unequivocally the exclusive trans-geometry of the 1,2-difluorovinyl moiety.

show abstract

Section: Introductionmentioning

confidence: 99%

Spectroscopic and Structural Assignment of the Absolute Stereochemistry in a Series of 1,2-Difluorovinyl Organometalloids. The First Crystallographic Characterization and Structural Series of Group 14 Fluorovinyl Compounds

et al. 2002

View full text Add to dashboard Cite

show abstract

“…We also examined the substitution of bromine atom for the vinylic silyl group . When 9c was treated with bromine, dibromide 11 was obtained in low yield due to its instability . Successive treatment of 9c with bromine and n -Bu 4 NF without isolation of 11 smoothly effected dibromination and elimination of a silyl bromide to give 2,2-difluorovinyl bromide 12 , a useful building block, in 87% yield (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

1-Trifluoromethylvinylsilane as a CF₂C^-−CH₂⁺ Synthon: Synthesis of Functionalized 1,1-Difluoro-1-alkenes via Isolable 2,2-Difluorovinylsilanes

2003

View full text Add to dashboard Cite

Various 1,1-difluoro-1-alkenes such as monosubstituted 1,1-difluoro-1-alkenes, 2-bromo-1,1-difluoro-1-alkenes, and 3,3-difluoroallylic alcohols are synthesized in two simple steps from 1-trifluoromethylvinylsilane: (i) its SN2' reaction with nucleophiles to construct 2,2-difluorovinylsilanes and (ii) the subsequent substitution of electrophiles for the vinylic silyl group. The combination of these two processes allows a one-pot synthesis of the functionalized 1,1-difluoro-1-alkenes starting from 1-trifluoromethylvinylsilane, which functions as a CF2=C(-)-CH2+ synthon.

show abstract

“…Allred and Rochow (2) have used the relative chemical shifts in the tetramethyl derivatives of the Group IV elements as the basis of an electronegativity scale. The 19F spectra of triethylperfluorovinylgermane (200), dimethyldiperfluorovinylgermane (41), and tetraperfluorovinylgermane (41) have been investigated, and the F-F coupling constants for these compounds calculated.…”

Section: E Mass Spectroscopymentioning

confidence: 99%

Organogermanium Chemistry.

Quane¹,

Bottei²

1963

Chem. Rev.

View full text Add to dashboard Cite

Vinyl Derivatives of Metals. XIII. Some Addition Reactions of Triethylperfluorovinylsilane: The F¹⁹ Nuclear Resonance Spectra of the Triethylperfluorovinyl Derivatives of Silicon, Germanium, and Tin and of Perfluorovinyltriethoxysilane

Cited by 15 publications

References 0 publications

Spectroscopic and Structural Assignment of the Absolute Stereochemistry in a Series of 1,2-Difluorovinyl Organometalloids. The First Crystallographic Characterization and Structural Series of Group 14 Fluorovinyl Compounds

Spectroscopic and Structural Assignment of the Absolute Stereochemistry in a Series of 1,2-Difluorovinyl Organometalloids. The First Crystallographic Characterization and Structural Series of Group 14 Fluorovinyl Compounds

1-Trifluoromethylvinylsilane as a CF₂C^-−CH₂⁺ Synthon: Synthesis of Functionalized 1,1-Difluoro-1-alkenes via Isolable 2,2-Difluorovinylsilanes

Organogermanium Chemistry.

Contact Info

Product

Resources

About

Vinyl Derivatives of Metals. XIII. Some Addition Reactions of Triethylperfluorovinylsilane: The F19 Nuclear Resonance Spectra of the Triethylperfluorovinyl Derivatives of Silicon, Germanium, and Tin and of Perfluorovinyltriethoxysilane

Cited by 15 publications

References 0 publications

Spectroscopic and Structural Assignment of the Absolute Stereochemistry in a Series of 1,2-Difluorovinyl Organometalloids. The First Crystallographic Characterization and Structural Series of Group 14 Fluorovinyl Compounds

Spectroscopic and Structural Assignment of the Absolute Stereochemistry in a Series of 1,2-Difluorovinyl Organometalloids. The First Crystallographic Characterization and Structural Series of Group 14 Fluorovinyl Compounds

1-Trifluoromethylvinylsilane as a CF2C-−CH2+ Synthon: Synthesis of Functionalized 1,1-Difluoro-1-alkenes via Isolable 2,2-Difluorovinylsilanes

Organogermanium Chemistry.

Contact Info

Product

Resources

About

Vinyl Derivatives of Metals. XIII. Some Addition Reactions of Triethylperfluorovinylsilane: The F¹⁹ Nuclear Resonance Spectra of the Triethylperfluorovinyl Derivatives of Silicon, Germanium, and Tin and of Perfluorovinyltriethoxysilane

1-Trifluoromethylvinylsilane as a CF₂C^-−CH₂⁺ Synthon: Synthesis of Functionalized 1,1-Difluoro-1-alkenes via Isolable 2,2-Difluorovinylsilanes