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Related Concept Videos

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.8K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
2.8K
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
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

11.8K
Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
11.8K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

2.7K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
2.7K
Cycloalkanes02:28

Cycloalkanes

12.7K
Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
12.7K
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

8.2K
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
8.2K

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Carbenes from cyclopropanated aromatics.

Alexander D Roth1, Dasan M Thamattoor1

  • 1Department of Chemistry, Colby College, Waterville, ME 04901, USA. dmthamat@colby.edu.

Organic & Biomolecular Chemistry
|November 23, 2023
PubMed
Summary
This summary is machine-generated.

Carbene chemistry research is advancing with new methods beyond traditional nitrogenous precursors. Cyclopropanated aromatic systems offer a safer, versatile alternative for generating diverse carbenes.

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms

Background:

  • Carbene chemistry is a well-established field with ongoing theoretical and experimental interest.
  • Traditional carbene generation methods involve thermal or photochemical decomposition of diazo compounds and diazirines.
  • These nitrogenous precursors can be hazardous, unavailable, or lead to side reactions in excited states.

Purpose of the Study:

  • To review alternative, non-traditional carbene generation methods.
  • To highlight the use of cyclopropanated aromatic systems as a carbene source.
  • To discuss the advantages and promise of these novel approaches.

Main Methods:

  • Utilizing cyclopropanated aromatic systems for carbene generation.
  • Employing cheletropic extrusion reactions.
  • Analyzing the formation of stable aromatic by-products.

Main Results:

  • A wide range of carbenes can be generated from cyclopropanated aromatic systems.
  • Stable aromatic by-products like phenanthrene, indane, naphthalene, and 1,4-dihydronaphthalene are formed.
  • This method provides a viable alternative to traditional carbene generation.

Conclusions:

  • Cyclopropanated aromatic systems represent a promising "non-traditional" source for carbene generation.
  • These methods offer versatility and potentially mitigate issues associated with diazo compounds and diazirines.
  • Further research into these novel carbene sources is warranted.