Samiksha Jaiswal (Editor)

9 Borabicyclo(3.3.1)nonane

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Abbreviations  9-BBN
Density  894 kg/m³
Formula  C8H15B
9-Borabicyclo(3.3.1)nonane httpsuploadwikimediaorgwikipediacommons33

9-Borabicyclo[3.3.1]nonane or 9-BBN is an organoborane compound. This colourless solid is used in organic chemistry as a hydroboration reagent. 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.

9-Borabicyclo(3.3.1)nonane CV9P0107gif

Preparation

9-BBN is prepared by the reaction of 1,5-cyclooctadiene and borane usually in ethereal solvents, for example:

9-Borabicyclo(3.3.1)nonane 9Borabicyclo331nonane Wikipedia

The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions.

9-Borabicyclo(3.3.1)nonane 9Borabicyclo331nonane Wikipdia

Its highly regioselective addition on alkenes allows the preparation of terminal alcohols 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.

9-Borabicyclo(3.3.1)nonane

References

9-Borabicyclo(3.3.1)nonane Wikipedia


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