9 bbn structure

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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. The compound is commercially available as a solution in tetrahydrofuran and as a solid. Its highly regioselective addition on alkenes allows the preparation of terminal alcohols by subsequent oxidative cleavage with H 2 O 2 in aqueous KOH. The steric demand of 9-BBN greatly suppresses the formation of the 2-substituted isomer compared to the use of borane. Contents move to sidebar hide.

9 bbn structure

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Other names Borabicyclononane Banana borane.

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Ramos uclm. The commercial 9-borabicyclo[3. Stoichiometric reactions, kinetic studies, and DFT calculations have allowed us to propose a plausible mechanism involving a heterocyclic amidinate intermediate with a three center-two electron B—H—B bond. Ramos, A. Carrillo-Hermosilla, R. To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

9 bbn structure

The hydroboration-oxidation of alkynes is similar to the reaction with alkenes. However, there is one important difference. The alkyne has two pi bonds and both are capable of reacting with borane BH 3. To limit the reactivity to only one of the pi bonds within the alkyne, a dialkyl borane reagent R 2 BH is used. Replacing two of the hydrogens on the borane with alkyl groups also creates steric hindrance so that the hydroboration reaction produces the regioselective,.

Barbara ponce library

Contents move to sidebar hide. Its highly regioselective addition on alkenes allows the preparation of terminal alcohols by subsequent oxidative cleavage with H 2 O 2 in aqueous KOH. English: Structural formula of monomeric 9-borabicyclo[3. Tools Tools. PMID Download as PDF Printable version. Captions Captions English Add a one-line explanation of what this file represents. Views View Edit History. You cannot overwrite this file. In other projects. Deutsch: Strukturformel von monomerem 9-Borabicyclo[3.

B -alkylBBN preparation is itself a two-step process, thus restricting the utility of the 9-BBN for synthetic purposes. These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Summary [ edit ] Description 9-BBN structure. Nature America, Inc. This colourless solid is used in organic chemistry as a hydroboration reagent. Organic Syntheses via Boranes. Categories : Organoboranes Reagents for organic chemistry. PMID English: Structural formula of monomeric 9-borabicyclo[3. Deutsch: Strukturformel von monomerem 9-Borabicyclo[3. Category : 9-BBN. EC Number. Read Edit View history. Download as PDF Printable version. Borabicyclononane Banana borane.