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Related Concept Videos

Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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9.4K
The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
9.4K
Carbocations02:10

Carbocations

14.4K
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Updated: Mar 19, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
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Enantioselective carbenoid insertion into C(sp(3))-H bonds.

J V Santiago1, A H L Machado1

  • 1Grupo de Tecnologia em Síntese Orgânica, Instituto de Química, Universidade de Brasília, Campus Universitário Darcy Ribeiro, 4478, CEP 70904-970, Asa Norte, Brasília-DF, Brasil.

Beilstein Journal of Organic Chemistry
|June 25, 2016
PubMed
Summary

Enantioselective carbenoid insertion into C(sp(3))-H bonds offers precise control for creating chiral molecules. This review covers early challenges, mechanisms, and modern uses of this synthetic chemistry technique.

Keywords:
C–H activationchiral catalysisdiazo compoundstotal synthesis

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Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis
  • Catalysis

Background:

  • Stereogenic centers are crucial in complex molecule synthesis.
  • Enantioselective reactions provide high control over stereochemistry.
  • Carbenoid insertion into C(sp(3))-H bonds is a key synthetic transformation.

Purpose of the Study:

  • To review the historical development of enantioselective carbenoid insertion into C(sp(3))-H bonds.
  • To discuss mechanistic insights into this reaction class.
  • To highlight recent advancements and applications in the field.

Main Methods:

  • Literature review of published research.
  • Analysis of mechanistic studies.
  • Compilation of recent synthetic applications.

Main Results:

  • Early challenges in controlling enantioselectivity were identified.
  • Mechanistic studies elucidated reaction pathways.
  • Recent applications demonstrate broad utility in synthesizing complex chiral molecules.

Conclusions:

  • Enantioselective carbenoid insertion is a powerful tool for stereoselective synthesis.
  • Continued research is expanding its scope and efficiency.
  • This methodology is vital for accessing enantiomerically pure compounds.