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Isomerisation of Alkenes Bearing Stannyl and Boryl Groups at the C=C Bond

  • Bernd Wrackmeyer EMAIL logo , Susanna Kerschl and Uwe Klaus
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 57 Issue 11

Alkenes bearing organometallic substituents such as boryl and stannyl groups isomerise slowly in the absence of UV irradiation. In addition to cis/trans isomerisation the boryl and stannyl group may also exchange places. This is shown for (Z)-2-chloro(dimethyl)stannyl-3-diethylboryl- pent-2-ene 5b (conversion into (Z)-3-chloro(dimethyl)stannyl-2-diethylboryl-pent- 2-ene 7b) and 3,4-diethyl-1,1,2,5-tetramethyl-1,2-dihydro-1,3-stannaborole8b (conversion into 3,5-diethyl-1,1,2,4-tetramethyl-1,2-dihydro-1,3-stannaborole 9b). Zwitterionic structures, involving a bridging boryl group with π-σ delocalisation, the stabilising effect exerted by a stannyl group in β-position with respect to a positively charged centre, and migration of a stannyl group, are suggested in oder to explain the isomerisation. The heterocycle 9b was prepared independently from the reaction of 7b with lithium diisopropylamide.

Keywords: Boron; Tin; Alkenes; Isomerisation; NMR Data
Received: 2002-8-14
Published Online: 2014-6-2
Published in Print: 2002-11-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

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  1. A Pyrazine-Bridged Ni(II) Coordination Polymer
  2. Synthesis and Structure of 1,3-Diisopropyl-4,5-dimethylimidazolium N,N'-Diphenylureate
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https://doi.org/10.1515/znb-2002-1109
Keywords for this article
Boron; Tin; Alkenes; Isomerisation; NMR Data

Articles in the same Issue

  1. A Pyrazine-Bridged Ni(II) Coordination Polymer
  2. Synthesis and Structure of 1,3-Diisopropyl-4,5-dimethylimidazolium N,N'-Diphenylureate
  3. Darstellung und Thermolyse tert-butylsubstituierter Silatetrazoline – Erzeugung der Silanimine tBu2Si=N-SiXtBu2 (X = F, Cl, Br, tBu) Synthesis and Thermolysis of the tert-Butyl-Substituted Silatetrazolines – Formation of the Silanimines tBu2Si=N-SiXtBu2 (X = F, Cl, Br, tBu)
  4. Synthesis and Reactivity of Cyclopentadienyl and Indenyl Ligands Bearing ω-Fluorinated Pendant Groups. Crystal Structure of (ortho-F-C6H4)-CPh2-C5H4SiMe3
  5. Ternary Antimonides YbTSb (T = Ni, Pd, Pt, Cu, Ag, Au) – Synthesis, Structure, Homogeneity Ranges, and 121Sb Mössbauer Spectroscopy
  6. Studies of Monothiomalonamide and its Palladium(II) and Platinum(II) Complexes
  7. Synthese, Kristallstruktur und Spektroskopische Charakterisierung des Phosphaniminato-Komplexes [Cl2AlNPCl3]2 und des Phosphanimin-Komplexes [Me3SiNPCl3 · AlCl3]/Synthesis, Crystal Structure, and Spectroscopic Characterization of the Phosphorane Iminato Complex [Cl2AlNPCl3]2, and of the Phosphane Imine Complex [Me3SiNPCl3 · AlCl3]
  8. Magnetic Exchange Based on π-π Stacking Interactions: Synthesis, Crystal Structure, Thermal Decomposition and Magnetic Properties of [Ce(phen)2(H2O)2(NO3)2](NO3)(phen)2(H2O)
  9. Isomerisation of Alkenes Bearing Stannyl and Boryl Groups at the C=C Bond
  10. Tetrapodal Pentadentate Ligands with NS4 and NP4 Donor Sets: An Elusive Tetrathiol, and a Sterically Encumbered Tetraphosphane
  11. K1.10Zr2Se6, Rb0.86Zr2Se6 and Cs0.80Zr2Se6. The First Intercalation Compounds of Zirconium Triselenide
  12. Neue Pnictide im CaAl2Si2-Typ und dessen Existenzgebiet/New Pnictides with the CaAl2Si2 Type Structure and the Stability Range of this Type
  13. Polysulfonylamine, CLXI. Ein neuartiges 1,2-Dihydroimidazochinolinylium-Kation: Zufällige Isolierung und Kristallstruktur des entsprechenden Dimesylamids Polysulfonylamines, CLXI. A Novel 1,2-Dihydroimidazoquinolinylium Cation: Serendipitous Isolation and Crystal Structure of the Corresponding Dimesylamide
  14. A New Trinuclear Cyano-Bridged Sr-Fe(III) Complex, [Sr2(phen)4(H2O)3(NO3)Fe(CN)6] · H2O
  15. Synthese difluorierter cyclopropanoider Nucleosidanaloga/Synthesis of Difluorinated Cyclopropanoid Nucleoside Analogues
  16. Orthoamide, LIX. Formyl-aalen [Tris(diformylamino)methan] – ein neues Formylierungsmittel für aktivierte Aromaten/Orthoamides, LIX. Formyl-aalen [Tris(diformylamino)methane] – a New Formylating Reagent for Activated Aromatic Compounds
  17. Molecular Complexes, 13. Weak Arene Complexes of Nitroaromatics. 1H NMR Studies of Conformations and Polar Effects. syn-anti Selectivity of 5-Nitrofurfural
  18. Crystal and Molecular Structure of 4-Arylhexahydro-1H,3H-pyrido[1,2-c]pyrimidine-1,3-dione Derivatives
  19. Kinetic Studies of Condensation of Aromatic Aldehydes with Meldrum’s Acid
  20. Bischler-Napieralski Synthesis of Some New Pyrazole-Fused β-Carbolines
  21. Novel and Facile Synthesis of Pyrazolo[3,4-d]pyrimidines
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