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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

IMPACT FACTOR 2018: 0.961

CiteScore 2018: 0.91

SCImago Journal Rank (SJR) 2018: 0.263
Source Normalized Impact per Paper (SNIP) 2018: 0.505

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Volume 63, Issue 11


1,2-Hydroboration of Alkyn-1-yldichlorosilanes using Triethylborane

Bernd Wrackmeyer / Ezzat Khan / Wolfgang Milius
Published Online: 2014-06-02 | DOI: https://doi.org/10.1515/znb-2008-1105


Triethylborane, BEt3, can act as a 1,2-hydroborating reagent towards alkyn-1-ylsilanes, depending on the nature of the silane. A mechanism is proposed invoking hydrogen transfer from the β -carbon of one ethyl group, quite different from the 1,2-hydroboration mechanism using tri-n-propylborane, BnPr3. The structure of the products has been confirmed by comparison with that obtained using 9-borabicyclo[3.3.1]nonane, 9-BBN, as a well established 1,2-hydroborating reagent. All products have been characterized by a consistent set of NMR data (1H, 11B, 13C and 29Si NMR). The molecular structure of (Z)-1-dichlorosilyl-1-[9-(9-borabicyclo[3.3.1]nonyl)]-2-phenylethene has been determined by single crystal X-ray diffraction.

Keywords: Alkynes; Alkenes; Triethylborane; 9-BBN; Silanes; Hydroboration; NMR

About the article

Received: 2008-07-28

Published Online: 2014-06-02

Published in Print: 2008-11-01

Citation Information: Zeitschrift für Naturforschung B, Volume 63, Issue 11, Pages 1267–1275, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2008-1105.

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© 1946 – 2014: Verlag der Zeitschrift für Naturforschung. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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