ChemInform Abstract: DIE SYNTH. DES TRIMETHYLAMINPYRROLYLOBORANS

Ioffe, Sema L.; Lyashenko, A. A.; Shitov, O. P.; Негребецкий, В. В.

doi:10.1002/chin.197206308

Cited by 1 publication

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“…Reaction of 1 equiv of pyrrole with a borane adduct is known to result in hydrogen elimination and formation of a pyrrole boron dihydride derivative such as ( N -pyrrolyl)BH 2 ·THF, , ( N -pyrrolyl)BH 2 ·NEt 3 , ( N -pyrrolyl)BH 2 ·(pyridine), , and ( N -pyrrolyl)BH 2 ·(imidazole) . Köster and Wrackmeyer reported that 3 equiv of pyrrole reacts with Et 3 N·BH 3 or THF·BH 3 with hydrogen elimination to yield tris( N -pyrrolyl)borane.…”

Section: Resultsmentioning

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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