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Carbocations02:10

Carbocations

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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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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
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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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.8K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
2.8K
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.
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1.8K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

2.4K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.4K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.1K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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A Lead(II) Substituted Triplet Carbene.

Fabian Dankert1, Julian Messelberger1, Ugo Authesserre1

  • 1Saarland University, Coordination Chemistry, Campus C4.1, D-66123 Saarbrücken, Germany.

Journal of the American Chemical Society
|October 18, 2024
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a lead-diazo compound that transforms into a triplet carbene upon irradiation. This carbene intermediate undergoes C-H bond insertion, offering insights into organometallic reaction mechanisms.

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Area of Science:

  • Organometallic Chemistry
  • Photochemistry
  • Carbene Chemistry

Background:

  • Pincer-type ligands are crucial for stabilizing reactive metal complexes.
  • Diazo compounds are versatile precursors for generating reactive intermediates.
  • Lead complexes are less explored compared to other transition metals.

Purpose of the Study:

  • To synthesize and characterize a novel lead-diazo compound.
  • To investigate the photolytic behavior of the lead-diazo complex.
  • To identify the resulting photoproduct and its reactivity.

Main Methods:

  • Synthesis of a pincer-type lead complex.
  • Reaction with a lithium diazo reagent.
  • Photochemical irradiation (UV/Vis spectroscopy).
  • Variable temperature NMR spectroscopy.
  • Quantum-chemical calculations.

Main Results:

  • Formation of a stable lead-diazo compound [L3Pb(C(═N2)TMS)][BArF24].
  • Photolysis yields a formal plumba-alkyne, identified as a metal-substituted triplet carbene.
  • The carbene intermediate undergoes intermolecular C-H bond insertion with toluene.

Conclusions:

  • The study demonstrates the successful synthesis and characterization of a lead-diazo complex.
  • Photochemical activation provides access to a unique metal-substituted triplet carbene.
  • This carbene exhibits reactivity, including C-H bond activation, opening new avenues in organolead chemistry.