Aryl(alkyl)hydrosilanes in reactions with m-nitrostyrene

Андрианов, К. А.; Sidorov, V. I.; Tartakovskaya, L. M.; Anpilogova, A. I.; Nepomnina, V. V.; Pushchevaya, K. S.

doi:10.1007/bf00862226

Cited by 3 publications

(3 citation statements)

References 2 publications

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“…The replacement of alkyl-substituted groups by aryl groups causes the slowing of the process rate, and the reaction basically proceeds in the direction of reduction. In the case of the addition of triphenylsilane, the reaction proceeds completely in the reduction direction: 12 Significant studies were carried out by Reikhsfield and Astrakhanov. 13,14 They investigated the kinetic regularity of the hydrosilylation of different hydrosilanes to arylalkenes (XC 6 H 4 CHACH 2 ) in the presence of platinum complexes.…”

Section: Introductionmentioning

confidence: 99%

Hydrosilylation reactions of methylhydridesiloxane to styrene and α‐methylstyrene

Mukbaniani

Tatrishvili

Titvinidze

et al. 2006

J of Applied Polymer Sci

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ABSTRACT:The hydrosilylation reaction of ␣,-bis(trimethylsiloxy)methylhydridesiloxane to styrene and ␣-methylstyrene in the presence of the catalyst platinum hydrochloric acid (a 0.1M solution in tetrahydrofuran) at a 1:35 ratio of initial compounds at various temperatures (80 -90°C) was investigated, and methylsiloxane oligomers with aryl-substituted groups in the side chain were obtained. Complete hydrosilylation of all active 'SiOH groups did not take place. The hydrosilylation reaction order, activation energies. and rate constants were determined. The synthesized oligomers were characterized by 1 H, 13 C, and IR spectral data. For the full characterization of the hydride addition of methylhydridesiloxane to styrene by the quantum-chemical half-empiric Austin Model 1 (AM1) method for all initial, intermediate, and final products, in the modeling of the hydrosilylation reaction of methyldimethoxysilane to styrene, the heats of formation, energy changes of the system depending on the change of distance between 'COSi' bonds, and the charge values on the atoms, dipole moments, and bond orders were calculated. The synthesized oligomers were characterized by gel permeation chromatography, differential scanning calorimetry, thermogravimetric analysis, and wide-angle X-ray diffraction.

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Section: Introductionmentioning

confidence: 99%

Hydrosilylation reactions of methylhydridesiloxane to styrene and α‐methylstyrene

Mukbaniani

Tatrishvili

Titvinidze

et al. 2006

J of Applied Polymer Sci

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“…The search for new nitro reduction methods has largely ignored the potential of silanes and siloxanes as reducing agents . During the 1970s, Andrianov and co-workers used several silanes for nitroarene reductions, but incomplete reactions and low yields were their norm. During this same period, Lipowitz and Bowman reported a single Pd/C-catalyzed reduction of nitrobenzene by polymethylhydrosiloxane (PMHS).…”

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confidence: 99%

Pd-Catalyzed Silicon Hydride Reductions of Aromatic and Aliphatic Nitro Groups

2005

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[reaction: see text] Room-temperature reduction of aromatic nitro groups to amines can be accomplished in high yield, with wide functional group tolerance and short reaction times (30 min) using a combination of palladium(II) acetate, aqueous potassium fluoride, and polymethylhydrosiloxane (PMHS). Replacing PMHS/KF with triethylsilane allows aliphatic nitro groups to be reduced to their hydroxylamines.

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“…This reaction may occur as a single concerted process without affecting the arguments given.) Attack on (I) would give the inactive dihydride, a stoicheiometric amount of SiR,(OEt), and no dihydrogen [equa- [FeH(SiR,) (6) and (7)] which by reaction with the silane [equation ( 3)] would regenerate (11), giving a catalytic loop. If reaction (6) or (7) were rate-determining and…”

Section: Resultsmentioning

confidence: 99%

Organosilicon chemistry. Part 25. Catalysis of the reaction between alcohols and silanes by hydrido-, dinitrogen-, and ethylene-iron complexes

Haszeldine¹,

Parish²,

Riley³

1980

J. Chem. Soc., Dalton Trans.

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The reaction between alcohols, ROH (R = Me, Et, Pin, or Bu"), and SiH(OEt), or SiPh,H, is strongly catalysed at room temperature by [FeH,(PMePh,),] or by [FeH,(N,)(PEtPh,),].With SiH(OEt),, reaction is complicated by alkoxy-exchange when R # OEt. With both catalysts the reactions have induction periods but are thereafter first order in the concentration of each of the reactants and of the catalyst. Mechanisms are proposed based on the formation of iron-silyl complexes. The complex [Fe(C,H,) (dppe),] (dppe = Ph,PCH,CH,PPh,) also catalyses the reaction but is rapidly deactivated by conversion into [FeH,(dppe),].

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Aryl(alkyl)hydrosilanes in reactions with m-nitrostyrene

Cited by 3 publications

References 2 publications

Hydrosilylation reactions of methylhydridesiloxane to styrene and α‐methylstyrene

Hydrosilylation reactions of methylhydridesiloxane to styrene and α‐methylstyrene

Pd-Catalyzed Silicon Hydride Reductions of Aromatic and Aliphatic Nitro Groups

Organosilicon chemistry. Part 25. Catalysis of the reaction between alcohols and silanes by hydrido-, dinitrogen-, and ethylene-iron complexes

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