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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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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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Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

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Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
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Complexometric Titration: Ligands00:43

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Different monodentate and polydentate ligands are used as complexing agents in complexometric titration reactions. The formation of complexes by mono- and bidentate ligands involves two or more intermediate steps, limiting their use as complexing agents. In comparison, polydentate ligands can form complexes with metal ions in a single-step process, facilitating sharper end points. This means polydentate ligands, such as amino carboxylic acid derivatives, are most commonly employed in...
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The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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High Resolution Physical Characterization of Single Metallic Nanoparticles
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Boronic acid and boronic ester containing polyoxometalates.

Hedi Karoui1, Chris Ritchie

  • 1School of Chemistry, The University of Melbourne, Parkville, Melbourne, Victoria 3010, Australia. critchie@unimelb.edu.au.

Dalton Transactions (Cambridge, England : 2003)
|November 17, 2016
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Summary

Researchers synthesized novel organoboron functionalized polyoxometalates using Schiff base chemistry. These new compounds, including boronic acid derivatives, were thoroughly characterized using various analytical techniques.

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Area of Science:

  • Inorganic Chemistry
  • Materials Science
  • Organometallic Chemistry

Background:

  • Polyoxometalates (POMs) are versatile inorganic clusters with diverse applications.
  • Functionalization of POMs with organoboron moieties can impart unique properties.
  • Schiff base chemistry offers a flexible route for synthesizing functionalized POMs.

Purpose of the Study:

  • To synthesize novel organoboron functionalized polyoxometalates.
  • To explore the utility of Schiff base chemistry in POM functionalization.
  • To characterize the synthesized compounds thoroughly.

Main Methods:

  • Synthesis of three organoboron functionalized polyoxometalates via Schiff base chemistry.
  • Characterization in the solid state using single crystal X-ray diffraction (XRD), FT-IR spectroscopy, and elemental analysis.
  • Characterization in solution using 1H NMR spectroscopy.

Main Results:

  • Successful synthesis of three distinct organoboron functionalized polyoxometalates: a boronic acid, its methyl ester, and its trimethylene glycol ester.
  • Confirmation of the structures and purity of the synthesized compounds through comprehensive analytical data.
  • Demonstration of the stability and solubility of the compounds in solution.

Conclusions:

  • Organoboron functionalized polyoxometalates can be effectively synthesized using Schiff base chemistry.
  • The synthesized compounds exhibit promising characteristics for further investigation in various applications.
  • The study highlights the potential of combining POMs and organoboron chemistry.