Introduction of Functional Silyl Groups into Tris(dialkylamino)phosphonium Methylides

Karl Heinz Dreihäupl, Hubert Schmidbaur

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Starting from tris(dialkylamino)phosphonium methylides (R2N)3PCH2 [1a: R = Me; 1b: R = Et] a series of silylated ylides with functional groups at the silicon substituents have been prepared (2 - 8). In the general formula X3Si-CH=P(NR2)3 the group SiX3 represents examples for X = Me, Cl, Br, OMe, iPrO, NMe2, but also for X3 = PhH2 etc. The compounds are prepared either via the transylidation reaction of 1a, b with reaction components X3SiY [Y = Cl, OTf], or through action of a base on the corresponding silylated phosphonium salts, following methods of preparation for non-functional silylated ylides. Bis(ylides) (9 - 12) are available along the same sequence of reactions, but employing difunctional silanes X2SiY2. Products of the type X2Si[CH=P(NR2)3]2 were investigated with X = Me, OMe, OEt, and NMe2. All ylides are thermally stable, distillable liquids, which have been identified via conventional spectroscopic methods. The ylides are versatile synthons in trans-silylation, trans-ylidation, and de-silylation reactions.

Original languageEnglish
Pages (from-to)669-673
Number of pages5
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Issue number6
StatePublished - Jun 1997
Externally publishedYes


  • Aminophosphines
  • Phosphorus Ylides
  • Silylation
  • Ylides


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