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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.
9-Borabicyclo(3.3.1)nonane (9-BBN), a reagent used in organic chemistry; The 3-letter code for Blackburn railway station in the UK; Blackburn railway station, Melbourne; Bengbu South railway station, China Railway pinyin code BBN; Raytheon BBN Technologies, formerly Bolt, Beranek and Newman, a technology company in Cambridge, Massachusetts
C 6 H 4 O 2 BH + HC 2 R → C 6 H 4 O 2 B-CHCHR. The product is a precursor to the Suzuki reaction and is the only borane which stops at the alkene instead of reacting further to the alkane. [3] [4] Catecholborane may be used as a stereoselective reducing agent when converting β-hydroxy ketones to syn 1,3-diols.
Disiamylborane (bis(1,2-dimethylpropyl)borane) is an organoborane with the formula [((CH 3) 2 CHCH(CH 3)) 2 BH] 2 (abbreviation: Sia 2 BH). It is a colorless waxy solid that is used in organic synthesis for hydroboration–oxidation reactions .
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