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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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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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α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
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Cycloaddition Reactions: Overview01:16

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Published on: April 19, 2019

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Uncommon carbene insertion reactions.

Ming-Yao Huang1, Shou-Fei Zhu1

  • 1Frontiers Science Center for New Organic Matter, State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University Tianjin 300071 China sfzhu@nankai.edu.cn.

Chemical Science
|January 13, 2022
PubMed
Summary
This summary is machine-generated.

Transition-metal-catalyzed carbene insertion reactions offer efficient C-C and C-heteroatom bond formation. This review highlights recent advances in "uncommon" carbene insertions, revealing their significant synthetic potential.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Transition-metal-catalyzed carbene insertion reactions are vital for constructing carbon-carbon and carbon-heteroatom bonds.
  • Common carbene insertions (e.g., into C-H, O-H bonds) are well-established, while uncommon insertions have been historically overlooked.

Purpose of the Study:

  • To review the historical development and recent advancements in uncommon transition-metal-catalyzed carbene insertion reactions.
  • To discuss the synthetic potential, applications, and challenges associated with these understudied reactions.

Main Methods:

  • Literature review of transition-metal-catalyzed carbene insertion reactions.
  • Focus on reactions involving uncommon bond insertions (B-H, Sn-H, Ge-H, P-H, F-H, C-C, M-M).

Main Results:

  • Recent studies demonstrate significant progress and synthetic utility in uncommon carbene insertion reactions.
  • These reactions offer new avenues for complex molecule synthesis.

Conclusions:

  • Uncommon carbene insertion reactions are emerging as powerful tools in organic synthesis.
  • Further exploration promises to unlock new applications and overcome existing challenges in this field.