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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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...
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Alkyl Halides02:45

Alkyl Halides

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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Halogenation of Alkenes02:46

Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Trifluoromethylated heterocycles.

Andrei A Gakh, Yuriy Shermolovich1

  • 1Oak Ridge National Laboratory, Oak Ridge, TN 37831, USA, The University of Virginia, Charlottesville, VA 22908, USA, The Discovery Chemistry Project, Bethesda, MD 20824, USA. gakhaa@yahoo.com.

Current Topics in Medicinal Chemistry
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Summary

This review covers modern synthetic methods for trifluoromethylated heterocycles, focusing on direct trifluoromethylation techniques. It highlights compounds with significant biomedical potential.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Heterocyclic Chemistry

Background:

  • This review builds upon previous work on monofluorinated heterocycles.
  • It focuses specifically on heterocycles featuring a single trifluoromethyl group directly attached to the ring.

Purpose of the Study:

  • To provide a comprehensive overview of the synthetic chemistry of trifluoromethylated heterocycles.
  • To emphasize recent advancements in direct trifluoromethylation methodologies.

Main Methods:

  • Catalytic reactions
  • Organometallic reagents
  • Carbene and hypervalent chemistry
  • Ionic nucleophilic and electrophilic trifluoromethylating agents

Main Results:

  • Detailed examination of modern direct trifluoromethylation methods.
  • Identification of key synthetic strategies for trifluoromethylated heterocycles.
  • Highlighting compounds with potential biomedical applications.

Conclusions:

  • Trifluoromethylated heterocycles are synthesized using diverse modern methods.
  • These compounds hold promise for biomedical applications.
  • Continued research in this area is crucial for drug discovery.