1,2-Dihydro-1,2-azaborine explained

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

Preparation

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]

Notes and 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. . 48 . 5 . January 2009 . 973–977 . 10.1002/anie.200805554 . A Hybrid Organic/Inorganic Benzene . A. J. V. Marwitz . M. H. Matus . L. N. Zakharov. D. A. Dixon . S.-Y. Liu . 19105174 . free .
3. TBS = tert-butyldimethylsilyl, step 2 RCM = ring-closing metathesis using Grubbs' catalyst, step 3 organic oxidation using palladium on carbon, step 4 reduction LiBHEt, 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