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Open AccessFeature PaperArticle

Insertion of Carbenes into Deprotonated nido-Undecaborane, B11H13(2-)

Department of Chemistry, University of Colorado, Boulder, CO 80309-0215, USA
Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 16610 Prague 6, Czech Republic
Author to whom correspondence should be addressed.
Academic Editors: Igor B. Sivaev, Narayan S. Hosmane and Bohumír Grűner
Molecules 2019, 24(20), 3779;
Received: 19 September 2019 / Revised: 9 October 2019 / Accepted: 9 October 2019 / Published: 21 October 2019
We have examined the insertion of carbenes carrying leaving groups into the [nido-B11H13]2− dianion to form the [closo-1-CB11H12] anion. The best procedure uses CF3SiMe3 and LiCl as the source of CF2. It is simple, convenient and scalable and proceeds with 70–90% yield. Density functional calculations have been used to develop a mechanistic proposal that accounts for the different behavior of CF2, requiring only one equivalent of base for successful conversion of Na[nido-B11H14] to [closo-1-CB11H12], and CCl2 and CBr2, which require more. View Full-Text
Keywords: carboranes; [closo-1-CB11H12] anion; difluorocarbene carboranes; [closo-1-CB11H12] anion; difluorocarbene
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MDPI and ACS Style

Pecyna, J.; Rončević, I.; Michl, J. Insertion of Carbenes into Deprotonated nido-Undecaborane, B11H13(2-). Molecules 2019, 24, 3779.

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