Home Physical Sciences 1,1-Ethylborationof Diethynyl(dimethyl)silane: Formation of a Silole Followed by [4+2]Cycloadditions to 7-Silanorbornadienes and 7-Silanorbornenes
Article
Licensed
Unlicensed Requires Authentication

1,1-Ethylborationof Diethynyl(dimethyl)silane: Formation of a Silole Followed by [4+2]Cycloadditions to 7-Silanorbornadienes and 7-Silanorbornenes

  • Bernd Wrackmeyer EMAIL logo and Jürgen Süß
Published/Copyright: June 2, 2014
Become an author with De Gruyter Brill
Author Information Explore this Subject
Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 57 Issue 7

Diethynyl(dimethyl)silane, Me2Si(C≡C-H)2 2, reacts with triethylborane, Et3B 1, by 1,1- ethylboration to give a silole, 3-diethylboryl-4-ethyl-1,1-dimethyl-sila-2,4-cyclopentadiene 3, as a short-lived intermediate which reacts further with 2 or dimerises via [4+2]cycloadditions to the 7-silanorbornadiene 4 or the 7-silanorbornene derivatives 5, respectively. Since the silole 3 was not detected by NMR, the analogous reactions were studied using 1-alkynyl(ethynyl)- dimethylsilanes, Me2Si(C≡C-H)C≡C-R 6 [R = Bu (a), iPent (b), tBu (c)]. In these cases, 1,1-ethylboration gave the siloles 7a,b,c and 7'a,b, now detected in the reaction solutions, and also 7-silanorbornadienes as [4+2]cycloaddition products. Major products were identified, and the progress of the reactions was monitored by NMR spectroscopy (1H, 11B, 13C and 29Si NMR).

Keywords: 1,1-Organoboration; Ethynylsilanes; Cycloaddition; NMRData
Received: 2002-4-4
Published Online: 2014-6-2
Published in Print: 2002-7-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Wechselwirkungen in Molekülkristallen, 179 [1, 2]. σ-Donator/Akzeptor-Komplexe {I2C=CI2···X⊖ } (X⊖ = Cl⊖ , Br⊖ , I⊖ , SCN⊖ ) von Tetraiodethen in Tetra(n-butyl)ammoniumhalogenid-Salzen / Interaction in Molecular Crystals, 179 [1, 2]. σ-Donor/Acceptor Complexes {I2C=CI2···X⊖} (X⊖= Cl⊖, Br⊖, I⊖, SCN⊖) of Tetraiodoethene in Tetra(n-butyl)ammonium Halide Salts
  2. Silanolato-Komplexe von Vanadium (III, IV) / Silanolato Complexes of Vanadium (III, IV)
  3. Improved Synthesis of HOPh2Si-SiPh2OH and Crystal Structure Analyses of HOPh2Si-SiPh2OH and HOPh2Si-SiPh2-O-Ph2Si-SiPh2OH·1/2C6H6
  4. Synthesis, Characterisation and Crystal Structure of a Cyano-Bridged Polymeric Yttrium-Iron Complex {[Y(phen)2(H2O)2Fe(CN)6]·8H2O}n
  5. 1,1-Ethylborationof Diethynyl(dimethyl)silane: Formation of a Silole Followed by [4+2]Cycloadditions to 7-Silanorbornadienes and 7-Silanorbornenes
  6. Octahedral Complexes of Fe(III) with Phosphorylic Ligands Closely Related to β-Diketones
  7. Double Porphyrin Platinum Conjugates
  8. Übergangsmetallorganisch stabilisierte Indate und Germanate: Synthese, Struktur und Eigenschaften der Komplexe [{(CO)5M}EX3]2– (M = Cr, Mo, W; E = In; X = Cl, Br), [(CO5Cr)InBr(μ2-Br)]22– sowie [{(CO)5Cr}E(oxinat)2]n– (E = In, n = 2; E = Ge, n = 1) / Organometallically Protected Indates and Germanates: Synthesis, Structure and Properties of [{(CO)5M}EX3]2- (M = Cr, Mo, W; E = In; X = Cl, Br), [(CO5Cr)InBr(μ2-Br)]22- and [{(CO)5Cr}E(oxinat)2]n- (E = In, n = 2; E = Ge, n = 1)
  9. A Homoleptic Zirconium Complex with Four Bulky η2-Pyrazolato Ligands
  10. Polysulfonylamine, CLV [1]. Starke und schwache Wasserstoffbrücken in den Kristallstrukturen von 2,2΄-Bipyridinium-, 1,10-Phenanthrolinium- und 1,8-Bis(dimethylamino)naphthalinium-dimesylamid / Polysulfonylamines, CLV [1]. Strong and Weak Hydrogen Bonding in the Crystal Structures of 2,2΄-Bipyridinium, 1,10-Phenanthrolinium and 1,8-Bis(dimethylamino)naphthalinium Dimesylamide
  11. Synthesis, Structure, and Magnetic Properties of CeNiIn2
  12. Ternary Indides LnRhIn2 (Ln = La, Ce, Pr, Nd, Sm) with MgCuAl2 Type Structure
  13. Palladium Complexes with Bidentate P,N Ligands: Synthesis, Characterization and Application in Ethene Oligomerization
  14. Metallkomplexe mit biologisch wichtigen Liganden, CXLVI [1]. Bis(allyl)-N,O-α-Aminocarboxylat-Rhodium-Komplexe / Metal Complexes of Biologically Important Ligands, CXLVI [1]. Bis(allyl)-N,O-α-Aminocarboxylate-Rhodium Complexes
  15. Borate, an Effective Mummification Agent in Pharaonic Egypt
  16. 2"-Chartreusin-monoacetate, a New Natural Product with Unusual Anisotropy Effects from the Marine Isolate Streptomyces sp. B5525, and its 4"-Isomer
  17. Synthesis and Crystal Structures of Two Monomeric Methylene Bis(diaminoalanes)
https://doi.org/10.1515/znb-2002-0705
Keywords for this article
1,1-Organoboration; Ethynylsilanes; Cycloaddition; NMRData

Articles in the same Issue

  1. Wechselwirkungen in Molekülkristallen, 179 [1, 2]. σ-Donator/Akzeptor-Komplexe {I2C=CI2···X⊖ } (X⊖ = Cl⊖ , Br⊖ , I⊖ , SCN⊖ ) von Tetraiodethen in Tetra(n-butyl)ammoniumhalogenid-Salzen / Interaction in Molecular Crystals, 179 [1, 2]. σ-Donor/Acceptor Complexes {I2C=CI2···X⊖} (X⊖= Cl⊖, Br⊖, I⊖, SCN⊖) of Tetraiodoethene in Tetra(n-butyl)ammonium Halide Salts
  2. Silanolato-Komplexe von Vanadium (III, IV) / Silanolato Complexes of Vanadium (III, IV)
  3. Improved Synthesis of HOPh2Si-SiPh2OH and Crystal Structure Analyses of HOPh2Si-SiPh2OH and HOPh2Si-SiPh2-O-Ph2Si-SiPh2OH·1/2C6H6
  4. Synthesis, Characterisation and Crystal Structure of a Cyano-Bridged Polymeric Yttrium-Iron Complex {[Y(phen)2(H2O)2Fe(CN)6]·8H2O}n
  5. 1,1-Ethylborationof Diethynyl(dimethyl)silane: Formation of a Silole Followed by [4+2]Cycloadditions to 7-Silanorbornadienes and 7-Silanorbornenes
  6. Octahedral Complexes of Fe(III) with Phosphorylic Ligands Closely Related to β-Diketones
  7. Double Porphyrin Platinum Conjugates
  8. Übergangsmetallorganisch stabilisierte Indate und Germanate: Synthese, Struktur und Eigenschaften der Komplexe [{(CO)5M}EX3]2– (M = Cr, Mo, W; E = In; X = Cl, Br), [(CO5Cr)InBr(μ2-Br)]22– sowie [{(CO)5Cr}E(oxinat)2]n– (E = In, n = 2; E = Ge, n = 1) / Organometallically Protected Indates and Germanates: Synthesis, Structure and Properties of [{(CO)5M}EX3]2- (M = Cr, Mo, W; E = In; X = Cl, Br), [(CO5Cr)InBr(μ2-Br)]22- and [{(CO)5Cr}E(oxinat)2]n- (E = In, n = 2; E = Ge, n = 1)
  9. A Homoleptic Zirconium Complex with Four Bulky η2-Pyrazolato Ligands
  10. Polysulfonylamine, CLV [1]. Starke und schwache Wasserstoffbrücken in den Kristallstrukturen von 2,2΄-Bipyridinium-, 1,10-Phenanthrolinium- und 1,8-Bis(dimethylamino)naphthalinium-dimesylamid / Polysulfonylamines, CLV [1]. Strong and Weak Hydrogen Bonding in the Crystal Structures of 2,2΄-Bipyridinium, 1,10-Phenanthrolinium and 1,8-Bis(dimethylamino)naphthalinium Dimesylamide
  11. Synthesis, Structure, and Magnetic Properties of CeNiIn2
  12. Ternary Indides LnRhIn2 (Ln = La, Ce, Pr, Nd, Sm) with MgCuAl2 Type Structure
  13. Palladium Complexes with Bidentate P,N Ligands: Synthesis, Characterization and Application in Ethene Oligomerization
  14. Metallkomplexe mit biologisch wichtigen Liganden, CXLVI [1]. Bis(allyl)-N,O-α-Aminocarboxylat-Rhodium-Komplexe / Metal Complexes of Biologically Important Ligands, CXLVI [1]. Bis(allyl)-N,O-α-Aminocarboxylate-Rhodium Complexes
  15. Borate, an Effective Mummification Agent in Pharaonic Egypt
  16. 2"-Chartreusin-monoacetate, a New Natural Product with Unusual Anisotropy Effects from the Marine Isolate Streptomyces sp. B5525, and its 4"-Isomer
  17. Synthesis and Crystal Structures of Two Monomeric Methylene Bis(diaminoalanes)
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2026 De Gruyter Brill
Downloaded on 1.3.2026 from https://www.degruyterbrill.com/document/doi/10.1515/znb-2002-0705/html
Scroll to top button