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Radical Formation: Abstraction00:47

Radical Formation: Abstraction

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The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
Even though homolysis produces radicals, it is different from radical...
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Hydrogen Bonds00:26

Hydrogen Bonds

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Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....
129.8K
Hydrogen Bonds01:04

Hydrogen Bonds

13.1K
A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
13.1K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
13.9K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

4.2K
A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
4.2K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.2K
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 reactions,...
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Hydrogen Production and Utilization in a Membrane Reactor
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Hydrogen-Atom Transfer Reactions.

Liang Wang1, Jian Xiao2

  • 1College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao, 266109, China.

Topics in Current Chemistry (Cham)
|August 31, 2016
PubMed
Summary
This summary is machine-generated.

The tert-amino effect enables direct functionalization of C(sp(3))-H bonds via hydrogen transfer and cyclization. This versatile strategy efficiently creates cyclic compounds using various catalysts and conditions.

Keywords:
C(sp3)–H functionalizationHeterocyclesHydrogen acceptorsHydrogen donorsHydrogen transfer

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • The tert-amino effect, a century-old concept, facilitates intramolecular hydrogen transfer/cyclization reactions.
  • Recent decades have seen significant advancements in this strategy for C-H bond functionalization.

Purpose of the Study:

  • To review and discuss the diverse applications of the [1,n]-hydrogen transfer/cyclization cascade.
  • To highlight the utility of this method in synthesizing various cyclic structures.

Main Methods:

  • Direct functionalization of inert C(sp(3))-H bonds into C-C, C-N, and C-O bonds.
  • Utilizing Lewis acids, Brønsted acids, organocatalysts, or thermal conditions.
  • Employing various hydrogen donors (e.g., methylene/methine adjacent to heteroatoms) and acceptors (e.g., activated alkynes, aldehydes).

Main Results:

  • Successful construction of 5-, 6-, and 7-membered heterocyclic and carbon rings.
  • High atom economy in the cyclization processes.
  • Demonstration of broad substrate scope for both hydrogen donors and acceptors.

Conclusions:

  • The [1,n]-hydrogen transfer/cyclization cascade is a powerful tool for synthesizing cyclic compounds.
  • This methodology offers efficient and versatile routes to complex molecular architectures.
  • The chapter provides a comprehensive overview of hydrogen donors and acceptors in this reaction class.