Jump to ContentJump to Main Navigation
Show Summary Details
More options …

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

Online
ISSN
1865-7117
See all formats and pricing
More options …
Volume 63, Issue 11

Issues

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

Abstract

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.

Export Citation

© 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

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Ezzat Khan, Bernd Wrackmeyer, Rhett Kempe, and Germund Glatz
Applied Organometallic Chemistry, 2015, Volume 29, Number 6, Page 384
[2]
Ezzat Khan, Bernd Wrackmeyer, Cristian Döring, and Rhett Kempe
European Journal of Inorganic Chemistry, 2014, Volume 2014, Number 21, Page 3411
[3]
Ezzat Khan, Oleg L. Tok, and Bernd Wrackmeyer
Applied Organometallic Chemistry, 2014, Volume 28, Number 4, Page 280
[4]
Ezzat Khan and Bernd Wrackmeyer
Open Chemistry, 2012, Volume 10, Number 5
[6]
Yuki Naganawa, Haiqing Guo, Kei Sakamoto, and Yumiko Nakajima
ChemCatChem, 2019, Volume 11, Number 16, Page 3756
[7]
Ezzat Khan, Rhett Kempe, and Bernd Wrackmeyer
Applied Organometallic Chemistry, 2009, Volume 23, Number 5, Page 204

Comments (0)

Please log in or register to comment.
Log in