Indole 3-sulfonium ylides and related sulfonium salts. Carbon and hydrogen nuclear magnetic resonance study

Park, Kyong Hwi; Gray, George A.; Daves, G. Doyle

doi:10.1021/ja00492a006

Cited by 18 publications

(5 citation statements)

References 3 publications

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“…Chemical shifts are reported relative to tetramethylsilane. Tentative 13 C NMR assignments are based on previously reported NMR assignments for polyindolylmethanes [11,12] as well as on NMR assignments of indole derivatives reported by Park et al [13]. In the reporting of NMR data, indole carbons are labeled C2-C7 with C3a and C7a indicating ring fusion positions.…”

Section: General Proceduresmentioning

confidence: 99%

Deprotonated diindolylmethanes as dianionic analogues of scorpionate bis(pyrazolyl)borate ligands: synthesis and structural characterization of representative titanocene and zirconocene complexes

Mason

Ogrin

Fneich

et al. 2005

Journal of Organometallic Chemistry

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Section: General Proceduresmentioning

confidence: 99%

Deprotonated diindolylmethanes as dianionic analogues of scorpionate bis(pyrazolyl)borate ligands: synthesis and structural characterization of representative titanocene and zirconocene complexes

Mason

Ogrin

Fneich

et al. 2005

Journal of Organometallic Chemistry

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“…11 B NMR chemical shifts are reported relative to Et 2 O·BF 3 . Tentative 13 C NMR assignments are based on previously reported NMR assignments for bis- and tris(3-methylindolyl)methanes as well as on NMR assignments of indole derivatives reported by Park and co-workers . In the reporting of NMR data, indole hydrogen and carbon atoms are referred to by the standard numbering scheme for indoles.…”

Section: Methodsmentioning

confidence: 99%

Planar, Three-Coordinate Boron Monohydrides Ligated by Bis(3-methylindolyl)methanes

2011

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Reactions of tris(3-methylindolyl)methane, bis(3-methylindolyl)-2-methoxyphenylmethane, and bis(3-methylindolyl)phenylmethane with THF·BH3 result in hydrogen elimination and yield the corresponding boron monohydride complexes (3-CH3C8H4NH)HC(3-CH3C8H4N)2BH (6), (2-CH3OC6H4)HC(3-CH3C8H4N)2BH (7), and PhHC(3-CH3C8H4N)2BH (8), respectively. Compositions and structures were confirmed by NMR (1H, 11B, 13C) and IR spectroscopy, elemental analysis, and X-ray crystallography. The molecular structures of 6–8 each possess a trigonal-planar boron atom which resides in the plane of a bidentate diindolylmethane ligand. This planarity, the lack of Lewis acid–base complexation in the presence of THF, and the short B–N distances suggest significant N→B π donation. Thermolysis of 6 did not produce the three-coordinate, pyramidal borane HC(3-CH3C8H4N)3B or a tripodal, four-coordinate acid–base complex, presumably due to the significant B–N π bonding in 6. The planarity of 6–8 and the isoelectronic relationship of BH to C: suggest that diindolylmethanes may be useful platforms for the preparation of a new family of N-heterocyclic carbenes.

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“…(2)]. [21] Once again, the strikingly facile access to this compound encouraged us to examine related substrates in more detail.…”

mentioning

confidence: 99%

A Direct Ylide Transfer to Carbonyl Derivatives and Heteroaromatic Compounds

2010

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Indole 3-sulfonium ylides and related sulfonium salts. Carbon and hydrogen nuclear magnetic resonance study

Cited by 18 publications

References 3 publications

Deprotonated diindolylmethanes as dianionic analogues of scorpionate bis(pyrazolyl)borate ligands: synthesis and structural characterization of representative titanocene and zirconocene complexes

Deprotonated diindolylmethanes as dianionic analogues of scorpionate bis(pyrazolyl)borate ligands: synthesis and structural characterization of representative titanocene and zirconocene complexes

Planar, Three-Coordinate Boron Monohydrides Ligated by Bis(3-methylindolyl)methanes

A Direct Ylide Transfer to Carbonyl Derivatives and Heteroaromatic Compounds

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