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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 BF ×Et O provided the first two examples of CAAC-BF 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-BF 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 (BH ) was readily formed in situ according to H and B 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. 3 2 3 3 3 1 11


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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: 30 Mar 2021 12:56
URI: http://d-scholarship.pitt.edu/id/eprint/17259

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