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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.
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]
2 BH 2 (CH 3) → BH(CH 3) 2 + 0.5 B 2 H 6. 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.
9-硼二环[3.3.1]壬烷 Metadata This file contains additional information, probably added from the digital camera or scanner used to create or digitize it.
A versatile dialkylborane is 9-BBN. Also called "banana borane", it exists as a dimer. 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. Hydroboration of alkenes with 9-BBN proceeds with excellent regioselectivity.
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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.