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Insertion of Carbenes into Deprotonated nido-Undecaborane, B11H13(2-)
J. Pecyna, I. Rončević, J. Michl,
Language English Country Switzerland
Document type Journal Article
Grant support
CESNET LM2015042
Czech National Grid Infrastructure
NLK
Directory of Open Access Journals
from 1997
Free Medical Journals
from 1997
PubMed Central
from 2001
Europe PubMed Central
from 2001
ProQuest Central
from 1997-01-01
Open Access Digital Library
from 1997-01-01
Medline Complete (EBSCOhost)
from 2009-03-01
Health & Medicine (ProQuest)
from 1997-01-01
- MeSH
- Lithium Chloride chemistry MeSH
- Hydrocarbons, Fluorinated chemical synthesis chemistry MeSH
- Molecular Structure MeSH
- Boron Compounds chemistry MeSH
- Publication type
- Journal Article MeSH
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.
References provided by Crossref.org
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- $a Pecyna, Jacek $u Department of Chemistry, University of Colorado, Boulder, CO 80309-0215, USA. Jacek.Pecyna@colorado.edu.
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- $a Insertion of Carbenes into Deprotonated nido-Undecaborane, B11H13(2-) / $c J. Pecyna, I. Rončević, J. Michl,
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- $a 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.
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- $a Michl, Josef $u Department of Chemistry, University of Colorado, Boulder, CO 80309-0215, USA. josef.michl@colorado.edu. Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 16610 Prague 6, Czech Republic. josef.michl@colorado.edu.
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