58307-46-3Relevant academic research and scientific papers
The reaction of (tert-Butoxysilyl)methylmagnesium chlorides with some organotin and organosilicon monochlorides
Bykova, Irina A.,Kisin, Alexander V.,Monin, Evgeny A.,Nosova, Valentina M.,Philippov, Alexander M.,Storozhenko, Pavel A.
, (2020/04/15)
Interaction between (tert-butoxysilyl)methylmagnesium chlorides of the general formula Me3-n(t-BuO)nSiCH2MgCl, n = 1–3, with some organotin and organosilicon monochlorides has been studied. It has been found that the reaction of the Grignard reagents with trialkyltin chlorides readily proceeds via the methylene carbon with the formation of C-substituted products Me3-n(t-BuO)nSiCH2SnR3, R = Me, n-Bu in high yields. The path of this reaction with Me3SiCl and MePh2SiCl depends on the structure of Grignard compound and chlorosilane electrophilicity. Increasing the number of the tert-butoxy groups in the Grignard reagent has unexpectedly been found to result in the formation of Me3-n(t-BuO)nSiCH2OSiMeR2, R = Me, Ph and decrease of the organosilylmethyl silicon compounds content in the reaction products. The structure of the compounds synthesized has been confirmed by 1H, 13C, 29Si, 117,119Sn NMR spectroscopy and mass spectrometry.
Synthesis and Hydrolysis of Alkoxy(aminoalkyl)diorganylsilanes of the Formula Type R2(RO)Si(CH2)nNH2 (R = Alkyl, n = 1-3): A Systematic Experimental and Computational Study
Ehbets, Julia,Lorenzen, Sabine,Mahler, Christoph,Bertermann, Rüdiger,Berkefeld, André,Poater, Jordi,Fritz-Langhals, Elke,Weidner, Richard,Bickelhaupt, F. Matthias,Tacke, Reinhold
, p. 1641 - 1659 (2016/04/26)
Alkoxy(aminoalkyl)silanes are important precursors for the formation of amino-functionalized polysiloxanes, which are used in many technical applications. To better understand the mechanism of the hydrolytic cleavage of the Si-alkoxy moiety of alkoxy(aminoalkyl)silanes (an important key step in the formation of amino-functionalized polysiloxanes), a systematic experimental and computational study on the hydrolysis of alkoxy(aminoalkyl)diorganylsilanes of the formula type R2(RO)Si(CH2)nNH2 (R = alkyl, n = 1-3) was conducted. For reasons of comparison, silanes of the formula types R2(RO)SiC(H)MeCH2NH2 and R2(RO)Si(CH2)nX [R = alkyl; n = 1-3; X = N(H)Me, NMe2, piperidino, NMe3+I-, N(H)COOMe, N(Me)COOMe] and compounds Me2(MeO)Si(CH2)6Me and Me2(MeO)Si(CH2)6NH2 were included in this study. For this purpose, the various silanes were synthesized and studied for their hydrolysis kinetics in CD3CN/D2O under acidic and basic conditions by using 1H NMR spectroscopy as the analytic tool. These experimental investigations were complemented by computational studies (calculation of proton affinities, reaction barriers, and energies relative to reactants of intermediate transition complexes). The different hydrolysis reactivities observed are the result of a number of parameters, such as electronic and steric effects, the strong impact of the pD value, and intramolecular N-H···O hydrogen bonds between the protonated amino group and the alkoxy leaving group. This comprehensive study provided deep insight into the mechanism of hydrolysis of analogous α-, β-, and γ-amino-functionalized alkoxy(aminoalkyl)diorganylsilanes of the formula type R2(RO)Si(CH2)nNH2 (R = organyl, n = 1-3) and a series of related α/β/γ analogues with other nitrogen-based functional groups.
METHOD OF PRODUCING ORGANOSILICON COMPOUND
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Page/Page column 7, (2009/12/23)
A method of producing an organosilicon compound includes substituting at least an OR1 group of a compound shown by the following general formula (1) to obtain a compound shown by the following general formula (2), [in-line-formulae]Si(OR1)3-mY1m—R2—Si(OR3)3-nY2n??(1)[/in-line-formulae] [in-line-formulae]Si(OR4)3-mY1m—R2—Si(OR4)3-nY2n??(2).[/in-line-formulae]
HETEROGENEOUS REACTIONS VII. FURTHER STUDIES ON THE HETEROGENEOUS GAS/SOLID REACTIONS OF SOLID ALKOXIDE BASES WITH VAPORIZED CHLOROMETHYLDIMETHYLHALOSILANES
Hopper, Steven P.,Tremelling, Michael J.,Goldman, Emma W.
, p. 247 - 256 (2007/10/02)
The results of the heterogeneous gas/solid reactions of chloromethyldimethylchloro (and fluoro)silane with solid lithium, sodium and potassium methoxide in the temperature range from 80-160 deg C are presented and discussed.Reaction with lithium methoxide serves as a clean, efficient high yield synthesis of chloromethyldimethylmethoxysilane without the complicating factors of side products or solvent to separate.The reactions of both the sodium and potassium methoxides lead to the displacement of halogen from silicon and to the displacement of the chloromethyl group.New evidence for the mechanism of the latter reaction is presented.With the potassium compound methylethyldimethoxysilane also is formed and a carbene, sila-olefin addition mechanism is suggested.Surprisingly, lithium t-butoxide did not react with the chlorosilane but did react with the fluorosilane to produce chloromethyldimethyl-t-butoxysilane in high purity and excellent yield.The reaction with potassium t-butoxide was more complicated, giving substitution for halogen and the chloromethyl group at silicon as well as t-butyl methyl ether.
