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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

8.1K
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 Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.8K
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.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
1.8K
Alkyl Halides02:45

Alkyl Halides

16.5K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
16.5K
Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

2.7K
Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
2.7K
Reactions of Acid Anhydrides01:19

Reactions of Acid Anhydrides

4.1K
The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid.
4.1K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

17.9K
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.
17.9K

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Updated: Jun 22, 2025

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

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f-Block hydride complexes - synthesis, structure and reactivity.

Richard Drummond Turnbull1, Nicola L Bell1

  • 1School of Chemistry, University of Glasgow, Glasgow, UK, G12 8QQ. Nicola.Bell@Glasgow.ac.uk.

Dalton Transactions (Cambridge, England : 2003)
|July 2, 2024
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F-block hydrides, compounds of the lightest and heaviest elements, are crucial for catalysis and materials science. Advances in synthesis and analysis enhance our understanding and manipulation of these versatile f-element compounds.

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Area of Science:

  • Inorganic Chemistry
  • Materials Science
  • Catalysis

Background:

  • F-block elements, the heaviest and lightest in the periodic table, form unique hydride compounds.
  • These f-block hydrides have diverse applications, including catalysis, light-responsive materials, and nuclear waste storage.
  • Recent synthetic and analytical advancements have improved the study and application of these compounds.

Purpose of the Study:

  • To provide an overview of f-block hydride chemistry.
  • To explore how f-elements influence hydride formation, structure, and reactivity.
  • To highlight the role of co-ligands in tuning hydride behavior for various applications.

Main Methods:

  • Review of binary metal hydrides.
  • Molecular solution phase studies on heteroleptic complexes.
  • Gas phase investigations.

Main Results:

  • F-element properties significantly impact hydride characteristics.
  • Co-ligands play a critical role in modulating hydride reactivity and function.
  • New synthetic and analytical techniques enable deeper understanding.

Conclusions:

  • F-block hydrides are a versatile class of compounds with significant potential.
  • Understanding the interplay between f-elements and ligands is key to unlocking new applications.
  • Continued research promises further innovation in catalysis, materials, and beyond.