Author/Authors :
Kazem D. Safa، نويسنده , , A. Hassan pour، نويسنده , , Mohammad H. Nasirtabrizi، نويسنده , , U. Mosaei Oskoei، نويسنده ,
Abstract :
The crowded dichlorosilane TsiSiEtCl2, (1), (Tsi = (Me3Si)3C) was prepared from the reaction between EtSiCl3 and TsiLi, then it was reduced with LiAlH4 to give TsiSiEtH2, (2). The hydride (2) was then treated with two equivalents of ICl/CCl4 or Br2/CCl4 to produce TsiSiEtI2, (3), and TsiSiEtBr2, (4), respectively. The reaction of compound (2) with one equivalent of ICl/CCl4 gives TsiSiEtHI, (5). This product reacted with H2O/dioxane in the presence of AgClO4 or with dry MeOH to produce TsiSiEtHOH, (6), and TsiSiEtHOMe, (7), respectively. The compound (3) reacted with H2O in DMSO/CH3CN to give TsiSiEt(OH)2, (8), and the compound TsiSiEtIOMe, (9), was prepared from the reaction of the compound (7) with ICl/CCl4. When the dichloride (1) was treated with NaOMe/MeOH it gave (Me3Si)2CHSiEt(OMe)2. It is suggested that the reaction proceeds through an elimination–addition mechanism. The dichloride (1) was also treated with KSCN, NaN3 or NaOCN in CH3CN to give SN2 substitution products. All the new products were characterized by FTIR, 1H NMR, and 13C NMR spectroscopy, mass spectrometry and elemental analysis.
Keywords :
Silicon , Steric hindrance , Trisyl , Organosilicon