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Related Concept Videos

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

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Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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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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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
1.4K

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Photochemical Oxidative Growth of Iridium Oxide Nanoparticles on CdSe@CdS Nanorods
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Reversible interconversion between a monomeric iridium hydroxo and a dinuclear iridium μ-oxo complex.

Richard J Burford1, Warren E Piers, Daniel H Ess

  • 1Department of Chemistry, University of Calgary , 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4.

Journal of the American Chemical Society
|February 7, 2014
PubMed
Summary

This study synthesizes novel iridium hydroxo complexes and a dinuclear iridium oxo complex. The findings reveal insights into the reversible formation of metal oxo moieties from metal hydroxo ligands, crucial for understanding catalytic processes.

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Catalysis Research

Background:

  • Metal hydroxo complexes are key intermediates in various catalytic reactions.
  • Understanding their transformation into metal oxo species is vital for mechanistic studies.
  • The synthesis and characterization of novel iridium complexes provide platforms for such investigations.

Purpose of the Study:

  • To synthesize and characterize novel monomeric iridium(I) hydroxo complexes.
  • To investigate the formation and structure of a dinuclear iridium oxo complex from the hydroxo precursor.
  • To elucidate the mechanism of phenolysis of the dinuclear iridium oxo complex.

Main Methods:

  • Synthesis of iridium hydroxo complexes via reaction of iridium chlorides with cesium hydroxide.
  • Characterization using NMR (31P, 1H), IR spectroscopy, and X-ray crystallography.
  • Kinetic studies employing varying phenol substrates and isotopic labeling (H/D).

Main Results:

  • Efficient synthesis of monomeric iridium(I) hydroxo complexes (5R) in high yields.
  • Formation of a dinuclear μ-oxo bridged iridium complex (6(iPr)) with a unique allene-like core.
  • Kinetic data indicate a bimolecular reaction mechanism for phenolysis, with protonation of the μ-oxo ligand as the rate-limiting step.

Conclusions:

  • The study successfully demonstrates the reversible condensation of metal hydroxo ligands to form metal oxo moieties.
  • The dinuclear iridium oxo complex serves as a valuable model for studying oxo ligand reactivity.
  • The findings offer a deeper understanding of reaction mechanisms involving metal-oxo intermediates in catalysis.