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

  • Karl-Heinz Dreihäupl and Hubert Schmidbaur
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 52 Issue 6

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 SiX 3 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.

Keywords: Silylation; Ylides; Phosphorus Ylides; Aminophosphines
Received: 1997-4-21
Published Online: 2014-6-2
Published in Print: 1997-6-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Introduction of Functional Silyl Groups into Tris(dialkylamino)phosphonium Methylides
  2. Bis(silylation) of Tris(dimethylamino)phosphonium Methylide
  3. Metal-Mediated Assembly of Hexameric Ethylcycloarsoxane (C2H5AsO)6 in Mono-and Dinuclear Complexes with Tetrahedral and Octahedral Coordination Spheres
  4. Quaternary Selenidogermanates(IV) A3[AgGe4Se10]·2H2O and A2[MnGe4Se10]·3H2O (A = Rb, Cs) with Open Framework Structures
  5. Vanadiumkomplexe mit dreizähnigen diaciden Liganden. Bis[2-(2′-hydroxyphenyl)-chinolin-8-olato]dimethoxo-dioxo-divanadium(V) -ein neuer Strukturtyp/Vanadium Complexes with Tridentate Diacidic Ligands. Bis[2-(2′-hydroxyphenyl)-8-quinolinolato)dimethoxo-dioxo-divanadium (V) - a New Structure Type
  6. Untersuchungen zur thermischen Zersetzung von Ammoniumlanthanhalogeniden/Investigation on the Thermal Decomposition of Ammonium Halides
  7. Darstellung und Charakterisierung der Carbosilazane Bis[tris(methylamino)silyl]methan und Bis[tris(phenylamino)silyl]methan/Preparation and Characterization of the Carbosilazanes Bis[tris(methylamino)silyl]methane and B is[tris(phenylamino)silyl]m ethane
  8. Laboratory Stopped-Flow XAFS Apparatus. Structure Determination of the Short-Lived Peroxochromium Intermediate Formed during Reduction Process of Chromate(VI) Ion by Hydrogen Peroxide
  9. Chemical Basis for High Activity in Oxygenation of Cyclohexane Catalyzed by Dinuclear Iron(III) Complexes with Ethereal Oxygen Containing Ligand and Hydrogen Peroxide System
  10. Synthese von Bis[pyridin-phthalocyaninato(1,5-)iridium(II)]iodid und Pyridin-iodo-phthalocyaninato(2-)iridium(III)-Pyridin durch schrittweise Oxydation von Bis[pyridin-phthalocyaninato(2-)iridium(II)]/Synthesis of Bis[pyridine-phthalocyaninato(1,5-)iridium(II)] Iodide and Pyridine-iodo-phthalocyaninato(2-)iridium(III)-Pyridine by Successive Oxidation of Bis[pyridine-phthalocyaninato(2-)iridium(II)]
  11. Zur Reaktion von N-Sulfonyliminodithiocarbonaten mit den Dibromiden des Cyclooctatetraens Reaction of Sulfonylcarboniminodithioates with the Dibromides of Cyclooctatetraene
  12. Novel Electrochemically Derived Dimers of Methylated Uracils
  13. Stereospecific Association of C-20 Epimers of 3β-Hydroxy-16-oxo-24-nor-17-azachol-5-eno-23-nitryle
  14. 1.3-Dithienium-and 1.3-Dithiolenium Salts, VI ,13C NMR Spectroscopic Investigations on 2-Substituted 1,3-Dithian-2-ylium Cations. Unusual γ-Effects
  15. Notizen: [{Cp*(CI)Re}2(μ-CO)2](Re ≡ Re), ein zweikerniger Rhenium(II)-Komplex mit cis-konfigurierten, terminalen Cl-Atomen/[{Cp*(Cl)Re}2(μ-CO)2](Re ≡ Re), a Dinuclear Rhenium(II) Complex with cis Configuration of the Terminal Cl Atoms
  16. Notizen: Synthese und Strukturuntersuchungen von Iodocupraten(I), XVIII. Darstellung und Kristallstruktur von PbCu2I4 ·2CH3CN/Synthesis and Structure Investigations of Iodocuprates(I), XVIII. Preparation and Crystal Structure of PbCu2I4 · 2CH3CN
  17. Notizen: Facile Preparation and Crystal Structure of [Bis(diphenylphosphino)amine]digold Dichloride
  18. Kristallstruktur von [PMePh3] [Cl - 1 - C≡C - Ph]/Crystal Structure of [PMePh3] [Cl - I - C≡C - Ph]
https://doi.org/10.1515/znb-1997-0601
Keywords for this article
Silylation; Ylides; Phosphorus Ylides; Aminophosphines

Articles in the same Issue

  1. Introduction of Functional Silyl Groups into Tris(dialkylamino)phosphonium Methylides
  2. Bis(silylation) of Tris(dimethylamino)phosphonium Methylide
  3. Metal-Mediated Assembly of Hexameric Ethylcycloarsoxane (C2H5AsO)6 in Mono-and Dinuclear Complexes with Tetrahedral and Octahedral Coordination Spheres
  4. Quaternary Selenidogermanates(IV) A3[AgGe4Se10]·2H2O and A2[MnGe4Se10]·3H2O (A = Rb, Cs) with Open Framework Structures
  5. Vanadiumkomplexe mit dreizähnigen diaciden Liganden. Bis[2-(2′-hydroxyphenyl)-chinolin-8-olato]dimethoxo-dioxo-divanadium(V) -ein neuer Strukturtyp/Vanadium Complexes with Tridentate Diacidic Ligands. Bis[2-(2′-hydroxyphenyl)-8-quinolinolato)dimethoxo-dioxo-divanadium (V) - a New Structure Type
  6. Untersuchungen zur thermischen Zersetzung von Ammoniumlanthanhalogeniden/Investigation on the Thermal Decomposition of Ammonium Halides
  7. Darstellung und Charakterisierung der Carbosilazane Bis[tris(methylamino)silyl]methan und Bis[tris(phenylamino)silyl]methan/Preparation and Characterization of the Carbosilazanes Bis[tris(methylamino)silyl]methane and B is[tris(phenylamino)silyl]m ethane
  8. Laboratory Stopped-Flow XAFS Apparatus. Structure Determination of the Short-Lived Peroxochromium Intermediate Formed during Reduction Process of Chromate(VI) Ion by Hydrogen Peroxide
  9. Chemical Basis for High Activity in Oxygenation of Cyclohexane Catalyzed by Dinuclear Iron(III) Complexes with Ethereal Oxygen Containing Ligand and Hydrogen Peroxide System
  10. Synthese von Bis[pyridin-phthalocyaninato(1,5-)iridium(II)]iodid und Pyridin-iodo-phthalocyaninato(2-)iridium(III)-Pyridin durch schrittweise Oxydation von Bis[pyridin-phthalocyaninato(2-)iridium(II)]/Synthesis of Bis[pyridine-phthalocyaninato(1,5-)iridium(II)] Iodide and Pyridine-iodo-phthalocyaninato(2-)iridium(III)-Pyridine by Successive Oxidation of Bis[pyridine-phthalocyaninato(2-)iridium(II)]
  11. Zur Reaktion von N-Sulfonyliminodithiocarbonaten mit den Dibromiden des Cyclooctatetraens Reaction of Sulfonylcarboniminodithioates with the Dibromides of Cyclooctatetraene
  12. Novel Electrochemically Derived Dimers of Methylated Uracils
  13. Stereospecific Association of C-20 Epimers of 3β-Hydroxy-16-oxo-24-nor-17-azachol-5-eno-23-nitryle
  14. 1.3-Dithienium-and 1.3-Dithiolenium Salts, VI ,13C NMR Spectroscopic Investigations on 2-Substituted 1,3-Dithian-2-ylium Cations. Unusual γ-Effects
  15. Notizen: [{Cp*(CI)Re}2(μ-CO)2](Re ≡ Re), ein zweikerniger Rhenium(II)-Komplex mit cis-konfigurierten, terminalen Cl-Atomen/[{Cp*(Cl)Re}2(μ-CO)2](Re ≡ Re), a Dinuclear Rhenium(II) Complex with cis Configuration of the Terminal Cl Atoms
  16. Notizen: Synthese und Strukturuntersuchungen von Iodocupraten(I), XVIII. Darstellung und Kristallstruktur von PbCu2I4 ·2CH3CN/Synthesis and Structure Investigations of Iodocuprates(I), XVIII. Preparation and Crystal Structure of PbCu2I4 · 2CH3CN
  17. Notizen: Facile Preparation and Crystal Structure of [Bis(diphenylphosphino)amine]digold Dichloride
  18. Kristallstruktur von [PMePh3] [Cl - 1 - C≡C - Ph]/Crystal Structure of [PMePh3] [Cl - I - C≡C - Ph]
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