9-Borabicyclo(3.3.1)nonane
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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.[1] 9-BBN is also known by its nickname 'banana borane'.[2] This is because rather than drawing out the full structure, chemists often simply draw a banana shape with the bridging boron.[3]Template:Better source
Preparation
9-BBN is prepared by the reaction of 1,5-cyclooctadiene and borane usually in ethereal solvents, for example:[4][5]
File:Synthesis of 9-BBN dimer.png
The compound is commercially available as a solution in tetrahydrofuran and as a solid. 9-BBN is especially useful in Suzuki reactions.[6][7][8]
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.
See also
References
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