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Novel method for preparing bis(trimethylsilyl) amines via treatment with trimethylsilylamines and methyl iodide

Authors
Journal
Journal of Organometallic Chemistry
0022-328X
Publisher
Elsevier
Publication Date
Volume
510
Identifiers
DOI: 10.1016/0022-328x(95)05821-6
Keywords
  • Silicon
  • Trimethylsilyl
  • N-(Trimethylsilyl)Diethylamine
  • Bissilylation
  • Bis(Trimethylsilyl)Amine

Abstract

Abstract A convenient method for the synthesis of N,N-bis(trimethylsilyl)alkylamines has been reported. N-(Trimethylsilyl)diethylamine incorporated with a stoichiometric amount of methyl iodide was effective to convert primary amines, especially aromatic amines, and their monotrimethylsilyl derivatives into the corresponding N,N-bis(trimethylsilyl)amine derivatives in high yields. In the case of N-trimethylsilyl derivatives of aliphatic primary amines, a half-amount of silylamines served as a silylation agent against another half-amount of silylamines in the presence of 0.5 equivalent of methyl iodide to give N,N-bis(trimethylsilyl)alkylamines in good yield. Allyl iodide, allyl bromide and benzyl bromide were also effective to promote the silylation activity of silylamines.

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