Chemistry:1,2-Dihydro-1,2-azaborine
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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. Several other 1,2-azaborines have been synthesized.[1]
Preparation
After decades of failed attempts, the compound was synthesized in 2008 and reported in January 2009.[2][3]
One of the synthetic steps is a ring-closing metathesis (RCM) reaction:[4]
1,2-Dihydro-1,2-azaborine synthesis Marwitz et al. 2009
References
- ↑ Dewar, Michael J. S.; Marr, Peter A. (1962-10-01). "A Derivative of Borazarene". Journal of the American Chemical Society 84 (19): 3782–3782. doi:10.1021/ja00878a045. ISSN 0002-7863. https://doi.org/10.1021/ja00878a045.
- ↑ 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
- ↑ 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.
- ↑ 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
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