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  2. Alpine borane - Wikipedia

    en.wikipedia.org/wiki/Alpine_borane

    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. Borylation - Wikipedia

    en.wikipedia.org/wiki/Borylation

    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 ...

  4. 9-Borabicyclo (3.3.1)nonane - Wikipedia

    en.wikipedia.org/wiki/9-Borabicyclo(3.3.1)nonane

    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]

  5. Organoboron chemistry - Wikipedia

    en.wikipedia.org/wiki/Organoboron_chemistry

    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.

  6. Boranes - Wikipedia

    en.wikipedia.org/wiki/Boranes

    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.

  7. File:9-BBN dimer structure.svg - Wikipedia

    en.wikipedia.org/wiki/File:9-BBN_dimer_structure.svg

    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.

  8. Catecholborane - Wikipedia

    en.wikipedia.org/wiki/Catecholborane

    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.

  9. 1,2,3,5-Tetrahydroxybenzene - Wikipedia

    en.wikipedia.org/wiki/1,2,3,5-Tetrahydroxybenzene

    It is a metabolite in the degradation of 3,4,5-trihydroxybenzoate (gallic acid) by Eubacterium oxidoreducens. [ 1 ] The enzyme pyrogallol hydroxytransferase uses 1,2,3,5-tetrahydroxybenzene and 1,2,3-trihydroxybenzene ( pyrogallol ), whereas its two products are 1,3,5-trihydroxybenzene ( phloroglucinol ) and 1,2,3,5-tetrahydroxybenzene.