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Related Concept Videos

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is stabilized by...
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
Fischer Projections02:18

Fischer Projections

Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines. While...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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.
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...

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Updated: Jun 3, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Why do some Fischer indolizations fail?

Nihan Çelebi-Ölçüm1, Ben W Boal, Alexander D Huters

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.

Journal of the American Chemical Society
|March 30, 2011
PubMed
Summary
This summary is machine-generated.

Fischer indole synthesis mechanisms were studied. Electron-donating groups favor N-N bond cleavage over the typical [3,3]-sigmatropic rearrangement pathway.

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry

Background:

  • The Fischer indole synthesis is a crucial reaction in organic chemistry for forming indole rings.
  • Understanding competing reaction pathways is essential for optimizing synthetic strategies.

Purpose of the Study:

  • To elucidate the detailed mechanisms of the Fischer indole synthesis.
  • To investigate the influence of substituents on reaction pathways and identify competing cleavage mechanisms.

Main Methods:

  • Utilized ab initio calculations, specifically SCS-MP2/6-31G(d), to model reaction energetics.
  • Incorporated aqueous solvation models to simulate reaction conditions.

Main Results:

  • Identified heterolytic N-N bond cleavage as a significant competing pathway.
  • Demonstrated that electron-donating substituents direct the reaction towards N-N bond cleavage.
  • Showed that these substituents inhibit the acid-promoted [3,3]-sigmatropic rearrangement.

Conclusions:

  • Substituent effects play a critical role in dictating the outcome of the Fischer indole synthesis.
  • The study provides a deeper mechanistic understanding, aiding in the rational design of indole synthesis protocols.