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CAAC boranes. synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF<inf>3</inf> and BH<inf>3</inf>

Monot, J and Fensterbank, L and Malacria, M and Laco̧te, E and Geib, SJ and Curran, DP (2010) CAAC boranes. synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF<inf>3</inf> and BH<inf>3</inf>. Beilstein Journal of Organic Chemistry, 6. 709 - 712. ISSN 1860-5397

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Abstract

In situ formation of two cyclic (alkyl) (amino) carbenes (CAACs) followed by addition of BF3×Et2O provided the first two examples of CAAC-BF3 complexes: 1-(2,6-diisopropylphenyl)-3,5,5- trimethyl-3-phenylpyrrolidin-2-ylidene trifluoroborane, and 2-(2,6- diisopropylphenyl)-3,3-dimethyl-2-azaspiro[4.5]decan-1-ylidene trifluoroborane. These CAAC-BF3 complexes are robust compounds that are stable to ambient laboratory conditions and silica gel chromatography. They were characterized by spectroscopy and X-ray crystallography. In contrast, a CAAC complex with borane (BH3) was readily formed in situ according to 1H and 11B NMR analysis, but did not survive the workup conditions. These results set the stage for further studies of the chemistry of CAAC boranes. © 2010 Monot et al.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Monot, J
Fensterbank, L
Malacria, M
Laco̧te, E
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Curran, DPcurran@pitt.eduCURRAN
Date: 2 August 2010
Date Type: Publication
Journal or Publication Title: Beilstein Journal of Organic Chemistry
Volume: 6
Page Range: 709 - 712
DOI or Unique Handle: 10.3762/bjoc.6.82
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1860-5397
Other ID: NLM PMC2956467
PubMed Central ID: PMC2956467
PubMed ID: 20978616
Date Deposited: 08 Feb 2013 21:00
Last Modified: 22 Jun 2021 12:56
URI: http://d-scholarship.pitt.edu/id/eprint/17259

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