110213-79-1Relevant academic research and scientific papers
The acid-induced rearrangement of 1-hydroxyalkyltris(trimethylsilyl)silanes
Sternberg, Katrin,Oehme, Hartmut
, p. 177 - 181 (2007/10/03)
In the presence of strong acids, such as HCl or H2SO4, 1-hydroxyalkyltris(trimethylsilyl)silanes (Me3Si)3Si-C(OH)R1-R2 (1a-f) isomerize by 1,2-Me3Si/OH exchange to give the trimethylsilylmethylsilanols (Me3Si)2Si(OH)-C(SiMe3)R1R 2 (4a-f) [R1,R2: a: Me, Me; b: H, 4-MeC6H4; c: H, 4-iPrC6H4; d: H, Mes; e: H, 2-Me2NC6H4; f: H, 2,4,6-(MeO)3C6H2]. A mechanism for the isomerization is proposed. In the case of the reaction of 1d with sulfuric acid, the silylsulfate (Me3Si)2-Si(OSO3H)-C(SiMe3)HMeS (5) was isolated. 5 is the intermediate in the H2SO4-catalyzed isomerization of 1d and was converted in situ with methanol, acetic anhydride, HF or HCl to give the respective methoxysilane 6, acetoxysilane 7, fluorosilane 8, or chlorosilane 9. Deprotonation of 4a, d, f with sodium hydride causes a further rearrangement, a 1,3-C,O-trimethylsilyl migration, to give the siloxanes (Me3Si)2(Me3. SiO)Si-CHR1R2 (11a, d, f).
ZUR WAGNER-MEERWEIN-ANALOGEN 1,2-SiMe3-VERSCHIEBUNG VON SILICIUM ZU KOHLENSTOFF BEI DER SPALTUNG VON METHYL-ETHERN
Maerkl, G.,Horn, M.,Schlosser, W.
, p. 4019 - 4022 (2007/10/02)
The ether-cleavage of methyl-ether as well as aryl(alkyl)-methyl-ether with BCl3, BBr3 isa accompanied by a 1,2-Me3Si-migration from silicon to carbon.
