Startseite Hydroboration of Bis(Trimethylsilyl)Ethyne. New Aspects of Hydroboration
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Hydroboration of Bis(Trimethylsilyl)Ethyne. New Aspects of Hydroboration

  • Bernd Wrackmeyer , Oleg. L. Tok , Wolfgang Milius , Moazzam H. Bhatti und Saqib Ali
Veröffentlicht/Copyright: 2. Juni 2014
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Zeitschrift für Naturforschung B
Aus der Zeitschrift Zeitschrift für Naturforschung B Band 58 Heft 1

Abstract

The hydroboration of bis(trimethylsilyl)ethyne, Me3Si-C≡C-SiMe3 1, with 9-borabicyclo [3.3.1] nonane (9-BBN) gives first the expected (Z)-alkene 5 which rearranges, without UV irradiation, after several days quantitatively into the (E)-alkene 6. Heating of 6 in the presence of a further equivalent of 1 leads, again almost quantitatively, to an allene, the 1,1,4,4-tetrakis(trimethylsilyl)-4-[9-(9- borabicyclo[3.3.1]nonyl)]buta-1,2-diene 8. Reactive structures arising from π-σ delocalisation involving the boryl group are proposed to be responsible both for the cis/trans-isomerisation and the allene formation. It is suggested that analogous structures may explain the previously observed formation of allenes 9 and 10, tin-analogues of 8. The structures of 5, 6 and 8 in solution follow from a consistent set of NMR data (1H, 11B, 13C, 29Si NMR), and the solid-state structure of 8 was confirmed by X-ray analysis.

Keywords: Alkynes; Alkenes; Allenes
Published Online: 2014-6-2
Published in Print: 2003-1-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Artikel in diesem Heft

  1. Dinuclear Derivatives of Mn2(CO)10 with the Ligand Tri(1-Cyclohepta- 2,4,6-Trienyl)Phosphane, P(C7H7)3, and their Oxidative Cleavage
  2. Synthesis and Reactivity of Bromo-Mer-Tricarbonyl-Trans-Bis[Tri(1-Cyclohepta- 2,4,6-Trienyl)Phosphane]-Manganese, Mnbr(CO)3[P(C7H7)3]2
  3. Transition Metal-Gallium Ordering In HfCoGa2 And HfNiGa2
  4. Metal Directed One-Pot Syntheses: Mono-, Di- and Tetra-Nuclear Clusters [1]
  5. Quadratate Und Hydrogenquadratate Cyclischer Stickstoffbasen Mit Schicht-, Ketten- und Leiterstrukturen / Squarates and Hydrogensquarates of Cyclic Nitrogen Bases with Layer-, Chainand Ladder-Structures
  6. Tungstenmethyl-Dimethylsilanols Cp(Oc)2(R3P)W—CH2—SiMe2OH (R = Me, Ph) – Synthesis Via Oxygenation or Hydrolysis
  7. Reaktionen von Vanadium(V)- und Tantal(V)-Komplexen Mit Kinetisch Stabilisierten Phosphaalkinen. Einfache Synthese von 1,3,4-Thia- und 1,3,4-Selenadiphospholen / Reactions of Vanadium(V) and Tantalum(V)-Complexes with Kinetically Stabilized Phosphaalkynes. A Simple Synthesis of 1,3,4-Thia and 1,3,4-Selenadiphospholes
  8. New Coordination Polymers Based On Transition Metal Squarates And Pyrazine Ligands
  9. Peri-Interactions in Naphthalenes, 9 [1]. On Hypercoordination in Non-Quaternary Phosphonium Salts and a Secondary Phosphine with the (8-Dimethylamino-Naphth-1-Yl) Substituent
  10. The Hexakis(N,N'-Dimethylurea)Cobalt(Ii) Cation: A Flexible Building Block for the Construction of Hydrogen Bonded Networks
  11. Metallkomplexe von Biologisch Wichtigen Liganden, CXLVIII [1]. Katalytische Peptidsynthese aus Glycinester miit Hilfe von Triflaten Und Cloriden der Seltenen Erden, sowie von Metall(III), (IV), (V) und (VI)-Chloriden / Metal Complexes of Biologically Important Ligands, CXLVIII [1]. Synthesis of Peptides from Glycine Ester Catalysed by Triflates and Chlorides of Metal(III, IV, V And VI) Ions
  12. Metallkomplexe mit Biologisch Wichtigen Liganden, CIL [1]. Metallorganische η2-N,O-Lysinato-Komplexe / Metal Complexes Of Biologically Important Ligands, Cil [1]. Organometallic η2-N,O-Lysinato-Complexes
  13. Synthese monofluorierter cyclopropanoider Nucleosidanaloga / Synthesis of Monofluorinated Cyclopropanoic Nucleoside Analogues
  14. Hydroxyurea Analogues of Fosmidomycin
  15. Synthesis of 2-Phenylisothiazol-3(2H)-One 1,1-Dioxides: Inhibitors of Human Leukocyte Elastase
  16. Erratum
  17. The Reduction of Pyridine to 1,4-Dihydropyridine by Lithiumtetrahydroborate in the Presence of Water
  18. Preparation, Crystal and Magnetic Structure of the Double Perovskites Ca2TWO6 (T = Co, Ni)
  19. Hydroboration of Bis(Trimethylsilyl)Ethyne. New Aspects of Hydroboration
  20. Conductivity, Electrodeposition and Magnetic Property of Cobalt(II) and Dysprosium Chloride in Zinc Chloride-1-Ethyl-3-Methylimidazolium Chloride Room Temperature Molten Salt
  21. A Zwitterionic Platinum Complex with a Carbene Ligand
  22. Synthesis and Structural Characterization of the Mixed Ligand Complex [Cu(Hml)2(Phen)] · 2 H2O (H2ml = 2-Methyllactic Acid)
  23. Synthesis, Thermal and X-Ray Investigations of the High-Temperature Phase of Copper(I) Cyanide
  24. Rietveld Refinement of the Crystal Structure of α-Be3N2 and the Experimental Determination of Optical Band Gaps for Mg3N2, Ca3N2 and CaMg2N2
  25. Preparation and Crystal Structure of Hexapotassium-μ-Oxo-Hexathiodititanate(IV), K6Ti2OS6
  26. (Phosphine)Silver(I) Sulfonate Complexes
  27. Beryllium Dichloride Coordination by Nitrogen Donor Molecules
  28. Zur gezielten Synthese funktionell substituierter Oligosilane aus Silyltriflaten und Aminosilyllithiumverbindungen / Tailor-Made Synthesis of Functional Substituted Oligosilanes from Silyl Triflates and (Aminosilyl)Lithium Compounds
  29. Secondary Bonding Interactionsi in Some Di- and Trihaloanilinium Halides
  30. Ba9[NbN4]2O[Cn2] – Synthesis, Crystal Structure and Raman Spectrum
https://doi.org/10.1515/znb-2003-0119
Schlagwörter für diesen Artikel
Alkynes; Alkenes; Allenes

Artikel in diesem Heft

  1. Dinuclear Derivatives of Mn2(CO)10 with the Ligand Tri(1-Cyclohepta- 2,4,6-Trienyl)Phosphane, P(C7H7)3, and their Oxidative Cleavage
  2. Synthesis and Reactivity of Bromo-Mer-Tricarbonyl-Trans-Bis[Tri(1-Cyclohepta- 2,4,6-Trienyl)Phosphane]-Manganese, Mnbr(CO)3[P(C7H7)3]2
  3. Transition Metal-Gallium Ordering In HfCoGa2 And HfNiGa2
  4. Metal Directed One-Pot Syntheses: Mono-, Di- and Tetra-Nuclear Clusters [1]
  5. Quadratate Und Hydrogenquadratate Cyclischer Stickstoffbasen Mit Schicht-, Ketten- und Leiterstrukturen / Squarates and Hydrogensquarates of Cyclic Nitrogen Bases with Layer-, Chainand Ladder-Structures
  6. Tungstenmethyl-Dimethylsilanols Cp(Oc)2(R3P)W—CH2—SiMe2OH (R = Me, Ph) – Synthesis Via Oxygenation or Hydrolysis
  7. Reaktionen von Vanadium(V)- und Tantal(V)-Komplexen Mit Kinetisch Stabilisierten Phosphaalkinen. Einfache Synthese von 1,3,4-Thia- und 1,3,4-Selenadiphospholen / Reactions of Vanadium(V) and Tantalum(V)-Complexes with Kinetically Stabilized Phosphaalkynes. A Simple Synthesis of 1,3,4-Thia and 1,3,4-Selenadiphospholes
  8. New Coordination Polymers Based On Transition Metal Squarates And Pyrazine Ligands
  9. Peri-Interactions in Naphthalenes, 9 [1]. On Hypercoordination in Non-Quaternary Phosphonium Salts and a Secondary Phosphine with the (8-Dimethylamino-Naphth-1-Yl) Substituent
  10. The Hexakis(N,N'-Dimethylurea)Cobalt(Ii) Cation: A Flexible Building Block for the Construction of Hydrogen Bonded Networks
  11. Metallkomplexe von Biologisch Wichtigen Liganden, CXLVIII [1]. Katalytische Peptidsynthese aus Glycinester miit Hilfe von Triflaten Und Cloriden der Seltenen Erden, sowie von Metall(III), (IV), (V) und (VI)-Chloriden / Metal Complexes of Biologically Important Ligands, CXLVIII [1]. Synthesis of Peptides from Glycine Ester Catalysed by Triflates and Chlorides of Metal(III, IV, V And VI) Ions
  12. Metallkomplexe mit Biologisch Wichtigen Liganden, CIL [1]. Metallorganische η2-N,O-Lysinato-Komplexe / Metal Complexes Of Biologically Important Ligands, Cil [1]. Organometallic η2-N,O-Lysinato-Complexes
  13. Synthese monofluorierter cyclopropanoider Nucleosidanaloga / Synthesis of Monofluorinated Cyclopropanoic Nucleoside Analogues
  14. Hydroxyurea Analogues of Fosmidomycin
  15. Synthesis of 2-Phenylisothiazol-3(2H)-One 1,1-Dioxides: Inhibitors of Human Leukocyte Elastase
  16. Erratum
  17. The Reduction of Pyridine to 1,4-Dihydropyridine by Lithiumtetrahydroborate in the Presence of Water
  18. Preparation, Crystal and Magnetic Structure of the Double Perovskites Ca2TWO6 (T = Co, Ni)
  19. Hydroboration of Bis(Trimethylsilyl)Ethyne. New Aspects of Hydroboration
  20. Conductivity, Electrodeposition and Magnetic Property of Cobalt(II) and Dysprosium Chloride in Zinc Chloride-1-Ethyl-3-Methylimidazolium Chloride Room Temperature Molten Salt
  21. A Zwitterionic Platinum Complex with a Carbene Ligand
  22. Synthesis and Structural Characterization of the Mixed Ligand Complex [Cu(Hml)2(Phen)] · 2 H2O (H2ml = 2-Methyllactic Acid)
  23. Synthesis, Thermal and X-Ray Investigations of the High-Temperature Phase of Copper(I) Cyanide
  24. Rietveld Refinement of the Crystal Structure of α-Be3N2 and the Experimental Determination of Optical Band Gaps for Mg3N2, Ca3N2 and CaMg2N2
  25. Preparation and Crystal Structure of Hexapotassium-μ-Oxo-Hexathiodititanate(IV), K6Ti2OS6
  26. (Phosphine)Silver(I) Sulfonate Complexes
  27. Beryllium Dichloride Coordination by Nitrogen Donor Molecules
  28. Zur gezielten Synthese funktionell substituierter Oligosilane aus Silyltriflaten und Aminosilyllithiumverbindungen / Tailor-Made Synthesis of Functional Substituted Oligosilanes from Silyl Triflates and (Aminosilyl)Lithium Compounds
  29. Secondary Bonding Interactionsi in Some Di- and Trihaloanilinium Halides
  30. Ba9[NbN4]2O[Cn2] – Synthesis, Crystal Structure and Raman Spectrum
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