Cyanoethylation of trichlorosilane

Petrov, A. D.; Миронов, В. Ф.; Vdovin, V. M.; Sadykh-Zade, S. I.

doi:10.1007/bf01177654

Cited by 3 publications

(6 citation statements)

References 2 publications

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“…Although molecular Pt complexes and Pt metal formed by reduction of them are often employed as the catalyst, there have been only a few reports on the hydrosilyation of carbonyl compounds using Pt catalyst. H 2 PtCl 6 promotes hydrosilyation of α,β-unsaturated aldehydes and ketones, accompanied by isomerization, to produce the silyl enol ether …”

Section: Resultssupporting

confidence: 60%

Triangular Triplatinum Complex with Four Bridging Si Ligands: Dynamic Behavior of the Molecule and Catalysis

et al. 2017

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A triangular triplatinum(0) complex with bridging diphenylsilylene ligands, [{(Pt(PMe 3 )} 3 (μ-SiPh 2 ) 3 ] (1a), reacts with H 2 SiPh 2 to produce the 1:1 adduct, [{Pt(PMe 3 )} 3 (H) 2 (μ-SiPh 2 ) 4 ] (2a), which was isolated and characterized by X-ray crystallography. Two Pt−Pt bonds of the triangular Pt 3 core are bridged by a diphenylsilylene ligand, while the remaining Pt−Pt bond has two unsymmetrical bridging Si ligands. Dissolution of 1a and H 2 SiPh 2 at a 1:3 molar ratio forms a mixture of complex 2a and unreacted 1a. NMR measurement of the solution at −90 °C revealed the structure of 2a as having two hydride ligands and four bridging silylene ligands. Two 31 P{ 1 H} NMR signals of 2a at −90 °C coalesce on warming to −50 °C owing to facile exchange of the four Si ligands. Reversible addition of H 2 SiPh 2 to 1a yielded 2a with ΔG°= −8.0 kJ mol −1 , ΔH°= −51.7 kJ mol −1 , and ΔS°= −146 J mol −1 K −1 . Addition of bis(4-fluorophenyl)silane and bis(4-methylphenyl)silane to the complexes, which have three bis(4-fluorophenyl)silylene and bis(4-methylphenyl)silylene ligands, respectively, also occurs reversibly in the solution, and the diarylsilane with an electron-withdrawing substituent is favored for the formation of Pt 3 Si 4 complexes. Complex 1a catalyzes hydrosilyation of benzaldehyde with H 2 SiPh 2 to produce diphenyl(benzyloxy)silane along with concurrent hydrosilyation and dehydrosilyation of phenyl(methyl)ketone. Dehydrogenative coupling of H 2 SiPh 2 and phenol is also catalyzed to yield diphenyl(phenoxy)silane. The 31 P{ 1 H} NMR spectra of the mixtures during the catalytic reaction show 2a as the major Pt-containing species.

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Section: Resultssupporting

confidence: 60%

Triangular Triplatinum Complex with Four Bridging Si Ligands: Dynamic Behavior of the Molecule and Catalysis

et al. 2017

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“…NMR Characterization of 1-Cyanobutadiene Dimers ( 220MHz, CDC13). Dimer A: 6.62 (t, «7 = 9,1 ), 6.02 (d, «7 = 10 Hz, t, «7 = 4 Hz, d, «7 = 2 Hz, 1H), 5.68 (m, 1 ), 5.50 (d, «7 = 9 Hz, 1H), 3.34 (s, 1+1/2 = 12 Hz, 1 ), 3.10 (t, =7 = 5 Hz, t, «7 = 10 Hz, 1 H), 2.23 (m, 2 ), 1.85 (m, 2 H). Dimer B: 6.39 (t, «7 = 9 Hz, 1 ), 6.00 (m, 1 H), 5.64 (m, 1H), 5.52 (d, «7 = 9 Hz, 1 ), 3.20 (m, 1 ), 3.10 (m, 1 ), 2.20 (m, 2 ), 1.84 (m, 1 ), 1.63 (m, 1 H).…”

Section: Methodsmentioning

confidence: 99%

“…Dimer A: 6.62 (t, «7 = 9,1 ), 6.02 (d, «7 = 10 Hz, t, «7 = 4 Hz, d, «7 = 2 Hz, 1H), 5.68 (m, 1 ), 5.50 (d, «7 = 9 Hz, 1H), 3.34 (s, 1+1/2 = 12 Hz, 1 ), 3.10 (t, =7 = 5 Hz, t, «7 = 10 Hz, 1 H), 2.23 (m, 2 ), 1.85 (m, 2 H). Dimer B: 6.39 (t, «7 = 9 Hz, 1 ), 6.00 (m, 1 H), 5.64 (m, 1H), 5.52 (d, «7 = 9 Hz, 1 ), 3.20 (m, 1 ), 3.10 (m, 1 ), 2.20 (m, 2 ), 1.84 (m, 1 ), 1.63 (m, 1 H). Dimer C: 6.68 (d, d, J = 16, 8 Hz, 1 ), 6.20 (m, 1 H), 5.68 (m, 1 H), 5.59 (d, J = 16 Hz, 1 H), 3.26 (d, J = 9 Hz, 1 H), 2.73 (m, 1 H), 2.23 (m, 2 ), 1.95 (m, 1 ), 1.61 (m, 1 H).…”

Section: Methodsmentioning

confidence: 99%

“…Dimer B: 6.39 (t, «7 = 9 Hz, 1 ), 6.00 (m, 1 H), 5.64 (m, 1H), 5.52 (d, «7 = 9 Hz, 1 ), 3.20 (m, 1 ), 3.10 (m, 1 ), 2.20 (m, 2 ), 1.84 (m, 1 ), 1.63 (m, 1 H). Dimer C: 6.68 (d, d, J = 16, 8 Hz, 1 ), 6.20 (m, 1 H), 5.68 (m, 1 H), 5.59 (d, J = 16 Hz, 1 H), 3.26 (d, J = 9 Hz, 1 H), 2.73 (m, 1 H), 2.23 (m, 2 ), 1.95 (m, 1 ), 1.61 (m, 1 H). Dimer D: 6.75 (d, d, J = 16,8 Hz, 1 H).…”

Section: Methodsmentioning

confidence: 99%

“…Two possibilities remain for the two isomers fluoro(fluorovinyl)cyclohexenes 15 and 16 as discussed previously. 6 The carbon NMR (Table I) is useful in distinguishing these possibilities.…”

Section: Palladium-catalyzed Hydrogenation Atmentioning

confidence: 99%

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Anti-Markovnikov terminal and gem-olefin hydrosilylation using a κ⁴-diimine nickel catalyst: selectivity for alkene hydrosilylation over ether C–O bond cleavage

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Cyanoethylation of trichlorosilane

Cited by 3 publications

References 2 publications

Triangular Triplatinum Complex with Four Bridging Si Ligands: Dynamic Behavior of the Molecule and Catalysis

Triangular Triplatinum Complex with Four Bridging Si Ligands: Dynamic Behavior of the Molecule and Catalysis

Dimerizations of electronegatively substituted dienes

Anti-Markovnikov terminal and gem-olefin hydrosilylation using a κ⁴-diimine nickel catalyst: selectivity for alkene hydrosilylation over ether C–O bond cleavage

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Cyanoethylation of trichlorosilane

Cited by 3 publications

References 2 publications

Triangular Triplatinum Complex with Four Bridging Si Ligands: Dynamic Behavior of the Molecule and Catalysis

Triangular Triplatinum Complex with Four Bridging Si Ligands: Dynamic Behavior of the Molecule and Catalysis

Dimerizations of electronegatively substituted dienes

Anti-Markovnikov terminal and gem-olefin hydrosilylation using a κ4-diimine nickel catalyst: selectivity for alkene hydrosilylation over ether C–O bond cleavage

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Anti-Markovnikov terminal and gem-olefin hydrosilylation using a κ⁴-diimine nickel catalyst: selectivity for alkene hydrosilylation over ether C–O bond cleavage