Bromo-di(silyl)methanes – Precursors to Disilylcarbanionic Ligands

Sebastian Bommers, Holger Beruda, Martin Paul, Hubert Schmidbaur

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The reaction of the series of methyl/phenylchlorosilanes Me2PhSiCl, MePh2SiCl and Ph3SiCl with CHBr3/n-BuLi to give the corresponding bromo-di(silyl)methanes has been investigated. The selectivity of the reaction proved to be strongly influenced by the number of phenyl groups bound to silicon. As already established for Me3SiCl, Si–C coupling readily occurs with Me2PhSiCl to give (Me2PhSi)2CHBr (1) in good yields, whereas MePh2SiCl affords (MePh2Si)2CHBr (2) in lower yields. The molecular structures of 2 and the by-product (MePh2Si)2CBr2have been determined by single crystal X-ray diffraction. In the case of the fully arylated species, Ph3SiCl, only the monosilylated compound (Ph3Si)CH2Br (3) is generated. (HMe2Si)2CHBr (5) can be obtained starting from 1 by treatment with triflic acid to give (CF3SO3Me2Si)2CHBr (4), followed by reduction of 4 with LiAlH4in diethyl ether. In situ metalation of 5 with n-BuLi affords (HMe2)2CHLi, which reacts instantaneously with a second equivalent of 5 to give the halogen-free dimer [(HMe2Si)2CH]SiMe2CH2SiMe2H (6).

Original languageEnglish
Pages (from-to)821-827
Number of pages7
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Issue number5
StatePublished - 1 May 1995
Externally publishedYes


  • Bromo-di(silyl)methanes
  • Chlorosilanes
  • Disilylmethanes


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