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9-Borabicyclo .3.1onane or 9-BBN is an organoborane compound. This colourless solid is used in organic chemistry as a hydroboration
The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions.
Its highly regioselective addition on alkenes allows the preparation of terminal
reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
. The compound exists as a hydride-bridged dimer, which easily cleaves in the presence of reducible substrates. 9-BBN is also known by its nickname 'banana borane'. This is because rather than drawing out the full structure, chemists often simply draw a banana shape with the bridging boron.
Preparation
9-BBN is prepared by the reaction of1,5-cyclooctadiene
Cycloocta-1,5-diene is a cyclic hydrocarbon with the chemical formula , specifically .
There are three configurational isomers with this structure, that differ by the arrangement of the four C–C single bonds adjacent to the double bonds. Each ...
and borane usually in ethereal solvents, for example:
The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions.
Its highly regioselective addition on alkenes allows the preparation of terminal alcohol
Alcohol most commonly refers to:
* Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom
* Alcohol (drug), an intoxicant found in alcoholic drinks
Alcohol may also refer to:
Chemicals
* Ethanol, one of sev ...
s by subsequent oxidative cleavage with H2O2 in aqueous KOH. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane.
See also
* Organoboron chemistry *Boron
Boron is a chemical element with the symbol B and atomic number 5. In its crystalline form it is a brittle, dark, lustrous metalloid; in its amorphous form it is a brown powder. As the lightest element of the ''boron group'' it has th ...
References
{{DEFAULTSORT:Borabicyclononane, 9- Organoboranes Reagents for organic chemistry