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Related Concept Videos

Catalysis02:50

Catalysis

The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the bromine molecule...
Catalysis01:27

Catalysis

Catalysis influences the rate of chemical reactions by providing an alternative reaction pathway with lower activation energy. A catalyst speeds up a reaction, but it is not consumed during the process. The fundamental principle of catalysis is the ability of a catalyst to alter the reaction mechanism, often introducing a more efficient pathway than the uncatalyzed process.In a catalyzed reaction, the catalyst participates directly in the reaction mechanism. It interacts with reactants to form...

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Related Experiment Video

Updated: Jul 19, 2026

Temperature-programmed Deoxygenation of Acetic Acid on Molybdenum Carbide Catalysts
08:15

Temperature-programmed Deoxygenation of Acetic Acid on Molybdenum Carbide Catalysts

Published on: February 7, 2017

A unique and highly efficient method for catalytic olefin aziridination.

Kiran Guthikonda1, J Du Bois

  • 1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.

Journal of the American Chemical Society
|November 15, 2002
PubMed
Summary

This study presents a new, efficient method for olefin aziridination using sulfamate esters and a rhodium catalyst. The process yields valuable aziridine intermediates for synthesizing 1,2-amine derivatives and primary amines.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Aziridination is a key transformation in organic synthesis.
  • Developing efficient and stereospecific methods for aziridination remains an active area of research.

Purpose of the Study:

  • To develop a facile, high-yielding, and stereospecific method for olefin aziridination.
  • To utilize sulfamate esters for N-atom transfer reactions.

Main Methods:

  • Employing sulfamate esters as nitrogen sources.
  • Utilizing 1-2 mol % Rh2(tfacam)4 as a catalyst.
  • Using PhI(OAc)2 as the terminal oxidant for N-atom transfer.
  • Reacting a diverse range of alkenes with H2NSO3CH2CCl3.

Main Results:

  • Achieved facile, high-yielding, and stereospecific olefin aziridination.
  • Synthesized alkoxysulfonyl aziridines as versatile intermediates.
  • Demonstrated smooth nucleophilic ring-opening of aziridines to 1,2-amine derivatives.
  • Successfully removed the N-trichloroethoxysulfonyl group to yield primary amines via mild reductive conditions.

Conclusions:

  • The described method offers an efficient and convenient approach for aziridination.
  • The resulting aziridine intermediates are valuable for synthesizing complex amine structures.
  • This chemistry provides a useful new tool for organic synthesis.