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Open Chemistry

formerly Central European Journal of Chemistry


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Volume 9, Issue 1

Issues

Volume 13 (2015)

Synthesis and NMR spectroscopic characterization of Si-substituted 1-silacyclobutene derivatives

Ezzat Khan
  • Anorganische Chemie II, Universität Bayreuth, D-95440, Bayreuth, Germany
  • Department of Chemistry University of Malakand, Chakdara, Dir(Lower), Khyber Pakhtunkhwa, Pakistan
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/ Bernd Wrackmeyer
Published Online: 2010-12-16 | DOI: https://doi.org/10.2478/s11532-010-0122-z

Abstract

Hydroboration of trialkyn-1-yl(organo)silanes with one equivalent and two equivalents of 9-borabicyclo[3.3.1]nonane, 9-BBN afford dialkyn-1-ylsilanes and alkyn-1-ylsilanes, respectively. The alkyn-1-ylsilane derivatives are stable at room temperature and can be store under dry argon for prolong period of time. These compounds are attractive materials for further rearrangements to afford novel 1-silacyclobutene derivatives bearing Si-alkenyl or Si-alkynyl functionalities. The hydroboration reaction is well controlled by the Si-R1 function, i.e., the starting silanes with R1 = Ph selectively afford hydroboration of one Si-C≡C bond with one equivalent of 9-BBN, leaving the other two functionalities untouched. Under mild reaction conditions (25°C), the starting silanes with R1 = Me lead to mixture containing dialkyn-1-ylsilane, alkyn-1-ylsilane and their respective 1-silacyclobutene derivatives. All new compounds are sensitive towards air and moisture and were studied by multinuclear magnetic resonance spectroscopy (1H, 13C, 11B, 29Si NMR) in solution.

Keywords: Alkynyl(organo)silanes; Hydroboration; Vinylboration; Silacyclobutenes; NMR

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About the article

Published Online: 2010-12-16

Published in Print: 2011-02-01


Citation Information: Open Chemistry, Volume 9, Issue 1, Pages 126–132, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-010-0122-z.

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© 2011 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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