Monomeric diphenylketiminodiphenylborane, a boron–nitrogen analogue of an allene

Jennings, J. R.; Pattison, I.; Summerford, C.; Wade, K.; Wyatt, B. K.

doi:10.1039/c1968000250b

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“…first examples of alkylideneaminoboranes. Information about their geometry and BNC bond order were obtained from IR data and X-ray structure analyses [2] . The results were complemented by theoretical studies [3] , which postulate a cumulene-like arrangement for the >CϭNϭB< group.…”

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Cyclic Ketiminoboranes

Weis¹,

Pritzkow

Siebert

1999

Eur. J. Inorg. Chem.

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The cyclocondensation reaction of benzil‐bis(trimethylsilylimin) (3) and Cl2B–NiPr2 via silicon‐boron exchangeresults in the solvent‐dependent formation of the 1,3,2‐diazaborole 1a or the 1,3,6,8,2,7‐tetraazadiborecin 2a. Using the more rigid 9,10‐bis(trimethylsilylimino)phenanthrene instead of 3 only the five‐membered heterocycle 4,5‐biphenylene‐2‐diisopropylamino‐1,3,2‐diazaborole (1b) is formed. The cyclic ketiminoboranes are characterized by NMR and X‐ray diffraction data. The 1,3,2‐diazaborole ring is almost planar, while the conformation of the 1,3,6,8,2,7‐tetraazadiborecin has the shape of a figure‐eight loop.

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“…of 1b single crystals suitable for an X-ray structure analysis were obtained. The two independent molecules in the cell 1a: 362 mg (2 mmol) of Cl 2 BN(iPr)2 dissolved in 10 mL of n-hexane was added dropwise within 50 min to a solution of 704 mg (2 show no significant difference. mmol) 3 in 20 mL of n-hexane at room temp.…”

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Cyclic Ketiminoboranes

Weis¹,

Pritzkow

Siebert

1999

Eur. J. Inorg. Chem.

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Boron‐Nitrogen Compounds 83 [1]. Experimental and Theoretical Studies on Monomeric Iminoboranes

Emerick

Nahm

Niedenzu

et al. 1980

Zeitschrift anorg allge chemie

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Nuclear magnetic resonance and vibrational spectroscopic data support the existence of liner CNB skeleton in monomeric iminoboranes of the type R2CNBR 2′. This allene‐like arrangement of the central moiety of the compounds does not seem to enhance the NB bond strength by interaction of this bond with the vicinal CN bond. Rather, in the case of R′ being a hydrocarbon group, the nature of the NB bond is similar to that found in (monoamino) diorganyl‐boranes, R2NBr 2′. Similarly, (CF3)2CNB[N(CH3)2]2 may ve viewed as a trisaminoborane. However, the rigid CNBN2 unit makes this compound colored and the electronic structure of the species was studied; theoretical and experimental data are in good agreement.

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The chemistry of iminoboranes

Meller¹

Inorganic and Analytical Chemistry

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Monomeric diphenylketiminodiphenylborane, a boron–nitrogen analogue of an allene

Cited by 3 publications

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Cyclic Ketiminoboranes

Cyclic Ketiminoboranes

Boron‐Nitrogen Compounds 83 [1]. Experimental and Theoretical Studies on Monomeric Iminoboranes

The chemistry of iminoboranes

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