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This reagent is generated by treating 9-BBN with α-pinene. [2] This sterically crowded chiral trialkylborane can stereoselectively reduce aldehydes in what is known as the Midland Alpine borane reduction, or simply the Midland reduction. [3] C 8 H 12 B-pinanyl + RCDO → C 8 H 12 BOCHDR + (+)-d-pinene. Hydrolysis of the resulting borinic ester ...
In the same year, M. M. Midland discovered B-3-alpha-pinanyl-9-BBN as the reducing agent, which could be easily available by reacting (+)-alpha-pinene with 9-BBN. The new reducing agent was later commercialized by Aldrich Co. under the name Alpine Borane and the asymmetric reduction of carbonyl groups with either enantiomer of Alpine-Borane is ...
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]
A versatile dialkylborane is 9-BBN. Also called "banana borane", it exists as a dimer. It can be distilled without decomposition at 195 °C (12mm Hg). Reactions with 9-BBN typically occur at 60–80 °C, with most alkenes reacting within one hour. Tetrasubstituted alkenes add 9-BBN at elevated temperature.
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With bulky substituents, primary and secondary boranes are more readily isolable and even useful. Examples include thexylborane and 9-BBN. Almost all primary and secondary boranes are dimeric with bridging hydrides.
The following other wikis use this file: Usage on ar.wikipedia.org 5،1-حلقي الأوكتاديين; Usage on cs.wikipedia.org 9-borabicyklo(3.3.1)nonan
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