1,2-Dihydro-1,2-azaborine

1,2-Dihydro-1,2-azaborine
Identifiers
ChemSpider 24769701 Y
Properties
Molecular formula C4H6BN
Molar mass 78.908 g mol−1
Appearance clear, colorless liquid
Melting point

−46 to −45 °C.
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,2-Dihydro-1,2-azaborine is an aromatic chemical compound with properties intermediate between benzene and borazine. Its chemical formula is C4BNH6. It resembles a benzene ring, except that two adjacent carbons are replaced by nitrogen and boron, respectively.

After decades of failed attempts, the compound was synthesized in 2008 and reported in January 2009.[1][2]

One of the synthetic steps is a ring-closing metathesis (RCM) reaction [3]:

References

  1. ^ Stu Borman. "Long-Sought Benzenelike Molecule Created: Aromaticity of organic-inorganic hybrid resembles benzene's." C&EN January 5, 2009 Volume 87, Number 01 p. 11
  2. ^ A. J. V. Marwitz, M. H. Matus, L. N. Zakharov, D. A. Dixon, S.-Y. Liu (January 2009). "A Hybrid Organic/Inorganic Benzene". Angew. Chem. Int. Ed. 48 (5): 973–977. doi:10.1002/anie.200805554. PMID 19105174. 
  3. ^ TBS = tert-butyldimethylsilyl, step 2 RCM = ring-closing metathesis using Grubbs' catalyst, step 3 organic oxidation using palladium on carbon, step 4 reduction LiBHEt3, step 5 conversion to piano stool complex as protective group with chromium carbonyl derivative, step 6 cleavage N-TBS bond HF, step 7 deprotection with triphenylphosphine