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Hydroboration-Oxidation of Alkenes03:08

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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A preorganized ditopic borane as highly efficient one- or two-electron trap.

Alexander Hübner1, Thomas Kaese1, Martin Diefenbach1

  • 1†Institut für Anorganische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, D-60438 Frankfurt am Main, Germany.

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|February 28, 2015
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Summary
This summary is machine-generated.

Researchers synthesized a red dianion salt and a dark green monoanion radical from bis(9-borafluorenyl)methane. These studies reveal direct B-B bonding interactions in the monoanion radical and dianion, confirmed by spectroscopy and crystallography.

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Area of Science:

  • Organoboron Chemistry
  • Supramolecular Chemistry
  • Spectroscopy and Crystallography

Background:

  • Bis(9-borafluorenyl)methane serves as a precursor for novel boron-containing compounds.
  • Understanding element-element bonding is crucial for developing new materials and reaction pathways.

Purpose of the Study:

  • To synthesize and characterize the dianion and monoanion radical of bis(9-borafluorenyl)methane.
  • To investigate the nature of boron-boron interactions in these reduced species.
  • To explore the reactivity of the dianion with protons.

Main Methods:

  • Chemical reduction using lithium metal.
  • Comproportionation reactions.
  • Electron Paramagnetic Resonance (EPR) spectroscopy.
  • X-ray crystallography.
  • Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Quantum-chemical calculations.

Main Results:

  • Synthesis of the red dianion salt Li2[1] and the dark green monoanion radical Li[1].
  • EPR spectroscopy confirmed hyperfine coupling to boron and protons, indicating unpaired electron localization.
  • X-ray crystallography revealed decreasing B···B distances (2.534(2) Å to 1.906(3) Å) with increasing reduction.
  • Protonation of Li2[1] yielded a cyclic borohydride with a B-H-B two-electron-three-center bond.
  • Computational analyses indicated localized B-B interactions in the reduced species.

Conclusions:

  • Direct B-B one-electron and two-electron bonding interactions are established in the monoanion radical and dianion, respectively.
  • The boron atoms exhibit nucleophilic character, enabling reactions like protonation of B-B bonds.
  • The study provides significant insights into bonding in reduced organoboron systems.