1,2-Dihydro-1,2-azaborine is an

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with properties intermediate between

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

and

borazine Borazine, also known as borazole, is a non-polar inorganic compound with the chemical formula B3H6N3. In this cyclic compound, the three BH units and three NH units alternate. The compound is isoelectronic and isostructural with benzene. For this ...

. 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. One of the synthetic steps is a

ring-closing metathesis Ring-closing metathesis (RCM) is a widely used variation of olefin metathesis in organic chemistry for the synthesis of various unsaturated rings via the intramolecular metathesis of two terminal alkenes, which forms the cycloalkene as the ''E-' ...

(RCM) reaction:TBS = tert-butyldimethylsilyl, step 2 RCM =

using

Grubbs' catalyst Grubbs catalysts are a series of transition metal carbene complexes used as catalysts for olefin metathesis. They are named after Robert H. Grubbs, the chemist who supervised their synthesis. Several generations of the catalyst have been develo ...

, step 3

organic oxidation Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations and reductions are different from ordinary redox reactions, because many reactions carr ...

using

palladium on carbon Palladium on carbon, often referred to as Pd/C, is a form of palladium used as a catalyst. The metal is supported on activated carbon to maximize its surface area and activity. Uses Hydrogenation Palladium on carbon is used for catalytic hydrog ...

, step 4 reduction LiBHEt, step 5 conversion to

piano stool complex Half sandwich compounds, also known as piano stool complexes, are organometallic complexes that feature a cyclic polyhapto ligand bound to an MLn center, where L is a unidentate ligand. Thousands of such complexes are known. Well-known examples in ...

protective group A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction. It plays an important role in multistep organic synthesis. In many ...

with chromium carbonyl derivative, step 6 cleavage N-TBS bond HF, step 7 deprotection with

triphenylphosphine Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists a ...

References

{{DEFAULTSORT:Dihydro-1, 2-azaborine, 1, 2- Aromatic compounds Boron heterocycles Nitrogen heterocycles Six-membered rings Boron–nitrogen compounds