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

  • Research Article
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Central European Journal of Chemistry

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.

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Authors and Affiliations

  1. Anorganische Chemie II, Universität Bayreuth, D-95440, Bayreuth, Germany

    Ezzat Khan & Bernd Wrackmeyer

  2. Department of Chemistry University of Malakand, Chakdara, Dir(Lower), Khyber Pakhtunkhwa, Pakistan

    Ezzat Khan

Authors
  1. Ezzat Khan
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  2. Bernd Wrackmeyer
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Correspondence to Ezzat Khan.

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Khan, E., Wrackmeyer, B. Synthesis and NMR spectroscopic characterization of Si-substituted 1-silacyclobutene derivatives. cent.eur.j.chem. 9, 126–132 (2011). https://doi.org/10.2478/s11532-010-0122-z

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  • DOI: https://doi.org/10.2478/s11532-010-0122-z

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