CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF3 and BH3
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]d...
Ausführliche Beschreibung
Autor*in: |
Julien Monot [verfasserIn] Louis Fensterbank [verfasserIn] Max Malacria [verfasserIn] Emmanuel Lacôte [verfasserIn] Steven J. Geib [verfasserIn] Dennis P. Curran [verfasserIn] |
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E-Artikel |
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Sprache: |
Englisch |
Erschienen: |
2010 |
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Schlagwörter: |
borane Lewis acid Lewis base complexes |
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Übergeordnetes Werk: |
In: Beilstein Journal of Organic Chemistry - Beilstein-Institut, 2005, 6(2010), 1, Seite 709-712 |
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Übergeordnetes Werk: |
volume:6 ; year:2010 ; number:1 ; pages:709-712 |
Links: |
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DOI / URN: |
10.3762/bjoc.6.82 |
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Katalog-ID: |
DOAJ013534394 |
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10.3762/bjoc.6.82 doi (DE-627)DOAJ013534394 (DE-599)DOAJ4a4b38223fe14225b9f47a3a0795c57a DE-627 ger DE-627 rakwb eng QD241-441 Julien Monot verfasserin aut CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF3 and BH3 2010 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. borane Lewis acid Lewis base complexes carbene–borane complexes cyclic (alkyl) (amino) carbenes N-heterocyclic carbenes stable carbenes Science Q Organic chemistry Louis Fensterbank verfasserin aut Max Malacria verfasserin aut Emmanuel Lacôte verfasserin aut Steven J. Geib verfasserin aut Dennis P. Curran verfasserin aut In Beilstein Journal of Organic Chemistry Beilstein-Institut, 2005 6(2010), 1, Seite 709-712 (DE-627)490226256 (DE-600)2192461-2 18605397 nnns volume:6 year:2010 number:1 pages:709-712 https://doi.org/10.3762/bjoc.6.82 kostenfrei https://doaj.org/article/4a4b38223fe14225b9f47a3a0795c57a kostenfrei https://doi.org/10.3762/bjoc.6.82 kostenfrei https://doaj.org/toc/1860-5397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_267 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 6 2010 1 709-712 |
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10.3762/bjoc.6.82 doi (DE-627)DOAJ013534394 (DE-599)DOAJ4a4b38223fe14225b9f47a3a0795c57a DE-627 ger DE-627 rakwb eng QD241-441 Julien Monot verfasserin aut CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF3 and BH3 2010 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. borane Lewis acid Lewis base complexes carbene–borane complexes cyclic (alkyl) (amino) carbenes N-heterocyclic carbenes stable carbenes Science Q Organic chemistry Louis Fensterbank verfasserin aut Max Malacria verfasserin aut Emmanuel Lacôte verfasserin aut Steven J. Geib verfasserin aut Dennis P. Curran verfasserin aut In Beilstein Journal of Organic Chemistry Beilstein-Institut, 2005 6(2010), 1, Seite 709-712 (DE-627)490226256 (DE-600)2192461-2 18605397 nnns volume:6 year:2010 number:1 pages:709-712 https://doi.org/10.3762/bjoc.6.82 kostenfrei https://doaj.org/article/4a4b38223fe14225b9f47a3a0795c57a kostenfrei https://doi.org/10.3762/bjoc.6.82 kostenfrei https://doaj.org/toc/1860-5397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_267 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 6 2010 1 709-712 |
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10.3762/bjoc.6.82 doi (DE-627)DOAJ013534394 (DE-599)DOAJ4a4b38223fe14225b9f47a3a0795c57a DE-627 ger DE-627 rakwb eng QD241-441 Julien Monot verfasserin aut CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF3 and BH3 2010 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. borane Lewis acid Lewis base complexes carbene–borane complexes cyclic (alkyl) (amino) carbenes N-heterocyclic carbenes stable carbenes Science Q Organic chemistry Louis Fensterbank verfasserin aut Max Malacria verfasserin aut Emmanuel Lacôte verfasserin aut Steven J. Geib verfasserin aut Dennis P. Curran verfasserin aut In Beilstein Journal of Organic Chemistry Beilstein-Institut, 2005 6(2010), 1, Seite 709-712 (DE-627)490226256 (DE-600)2192461-2 18605397 nnns volume:6 year:2010 number:1 pages:709-712 https://doi.org/10.3762/bjoc.6.82 kostenfrei https://doaj.org/article/4a4b38223fe14225b9f47a3a0795c57a kostenfrei https://doi.org/10.3762/bjoc.6.82 kostenfrei https://doaj.org/toc/1860-5397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_267 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 6 2010 1 709-712 |
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10.3762/bjoc.6.82 doi (DE-627)DOAJ013534394 (DE-599)DOAJ4a4b38223fe14225b9f47a3a0795c57a DE-627 ger DE-627 rakwb eng QD241-441 Julien Monot verfasserin aut CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF3 and BH3 2010 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. borane Lewis acid Lewis base complexes carbene–borane complexes cyclic (alkyl) (amino) carbenes N-heterocyclic carbenes stable carbenes Science Q Organic chemistry Louis Fensterbank verfasserin aut Max Malacria verfasserin aut Emmanuel Lacôte verfasserin aut Steven J. Geib verfasserin aut Dennis P. Curran verfasserin aut In Beilstein Journal of Organic Chemistry Beilstein-Institut, 2005 6(2010), 1, Seite 709-712 (DE-627)490226256 (DE-600)2192461-2 18605397 nnns volume:6 year:2010 number:1 pages:709-712 https://doi.org/10.3762/bjoc.6.82 kostenfrei https://doaj.org/article/4a4b38223fe14225b9f47a3a0795c57a kostenfrei https://doi.org/10.3762/bjoc.6.82 kostenfrei https://doaj.org/toc/1860-5397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_267 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 6 2010 1 709-712 |
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10.3762/bjoc.6.82 doi (DE-627)DOAJ013534394 (DE-599)DOAJ4a4b38223fe14225b9f47a3a0795c57a DE-627 ger DE-627 rakwb eng QD241-441 Julien Monot verfasserin aut CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF3 and BH3 2010 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. borane Lewis acid Lewis base complexes carbene–borane complexes cyclic (alkyl) (amino) carbenes N-heterocyclic carbenes stable carbenes Science Q Organic chemistry Louis Fensterbank verfasserin aut Max Malacria verfasserin aut Emmanuel Lacôte verfasserin aut Steven J. Geib verfasserin aut Dennis P. Curran verfasserin aut In Beilstein Journal of Organic Chemistry Beilstein-Institut, 2005 6(2010), 1, Seite 709-712 (DE-627)490226256 (DE-600)2192461-2 18605397 nnns volume:6 year:2010 number:1 pages:709-712 https://doi.org/10.3762/bjoc.6.82 kostenfrei https://doaj.org/article/4a4b38223fe14225b9f47a3a0795c57a kostenfrei https://doi.org/10.3762/bjoc.6.82 kostenfrei https://doaj.org/toc/1860-5397 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_267 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 6 2010 1 709-712 |
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CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF3 and BH3 |
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. |
abstractGer |
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. |
abstract_unstemmed |
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. |
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CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino) carbene borane complexes from BF3 and BH3 |
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