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Related Concept Videos

Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of Amides01:29

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

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Related Experiment Video

Updated: May 21, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Direct chemical method for preparing 2,3-epoxyamides using sodium chlorite.

Lilia Fuentes1, Urbano Osorio, Leticia Quintero

  • 1Centro de Investigación de la Facultad de Ciencias Químicas, BUAP, 14 Sur Esq. San Claudio, San Manuel, 72570, Puebla, México.

The Journal of Organic Chemistry
|June 6, 2012
PubMed
Summary

A new direct method prepares 2,3-epoxyamides from tertiary allylamines using sodium chlorite. This tandem C-H oxidation and epoxidation reaction offers a straightforward route to valuable chemical intermediates.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Tertiary allylamines are versatile precursors in organic synthesis.
  • Efficient methods for synthesizing 2,3-epoxyamides are crucial for accessing complex molecules.

Purpose of the Study:

  • To develop a direct and efficient method for preparing 2,3-epoxyamides.
  • To investigate a tandem C-H oxidation/double bond epoxidation strategy.

Main Methods:

  • Utilizing sodium chlorite for a two-step reaction: allylic oxidation followed by epoxidation.
  • In situ generation of hypochlorite ion for the epoxidation step.
  • Exploring functional group tolerance under the reaction conditions.

Main Results:

  • Successful preparation of 2,3-epoxyamides from tertiary allylamines.
  • Demonstrated tolerance of various functional groups including hydroxyl, TBS, aryl, alkyl, allyl, acetyl, and benzyl.
  • Identified the need for a scavenger when using activated aromatic rings.

Conclusions:

  • The reported method provides a direct and effective route to 2,3-epoxyamides.
  • The reaction's functional group tolerance makes it applicable to diverse substrates.
  • Further optimization may be needed for substrates with activated aromatic rings.