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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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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...
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Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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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...
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Preparation of Epoxides03:00

Preparation of Epoxides

9.0K
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...
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C–C Bond Cleavage: Retro-Aldol Reaction00:57

C–C Bond Cleavage: Retro-Aldol Reaction

7.4K
The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
7.4K
Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

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Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
6.7K
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

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Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain...
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Methods and applications for epoxide C-C bond cleavage reactions.

Noam Orbach1, Zachary P Sercel1, Rahul Suresh1

  • 1Schulich Faculty of Chemistry and the Resnick Sustainability Center for Catalysis, Technion - Israel Institute of Technology, Technion City, Haifa, Israel.

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Summary

Epoxides offer unique C-C bond cleavage reactions beyond typical C-O bond breaking. These transformations enable the synthesis of complex oxygenated molecules, expanding synthetic chemistry toolkits.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • Epoxides are versatile synthetic intermediates, commonly utilized for C-O bond cleavage reactions.
  • Conventional epoxide chemistry primarily focuses on nucleophilic attack at the epoxide carbons, leading to C-O bond scission.

Purpose of the Study:

  • To review and highlight the diverse modes of C-C bond cleavage reactions involving epoxides.
  • To showcase the synthetic utility of these underutilized epoxide C-C bond cleavage strategies.
  • To suggest future research directions for developing novel epoxide C-C bond cleavage transformations.

Main Methods:

  • Discussion of various catalytic and non-catalytic reaction mechanisms for epoxide C-C bond cleavage.
  • Compilation of reported synthetic applications demonstrating the construction of complex molecular architectures.
  • Analysis of orthogonal conditions that favor C-C over C-O bond cleavage.

Main Results:

  • Epoxides can undergo selective C-C bond cleavage through various transformations, often under conditions orthogonal to C-O bond cleavage.
  • These C-C bond cleavage reactions provide access to diverse oxygenated cyclic and acyclic compounds.
  • Established methods demonstrate significant synthetic utility in constructing challenging molecular frameworks.

Conclusions:

  • Epoxide C-C bond cleavage represents a powerful and underutilized synthetic strategy.
  • Further development of these methods promises to expand the scope of epoxide transformations in organic synthesis.
  • These reactions offer efficient routes to valuable oxygenated molecules.