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Preparation of Epoxides03:00

Preparation of Epoxides

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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...
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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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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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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.2K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Sharpless Epoxidation02:57

Sharpless Epoxidation

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The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
4.2K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.4K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Semiochemicals via epoxide inversion.

J E Oliver1, R M Waters, D J Harrison

  • 1Insect Chemical Ecology Laboratory Beltsville Agricultural Research Center Agricultural Research Service, USDA, 20705, Beltsville, Maryland.

Journal of Chemical Ecology
|November 15, 2013
PubMed
Summary
This summary is machine-generated.

This study introduces a novel reaction sequence to invert the stereochemistry of both epoxide carbons in 1,2-disubstituted epoxides, enabling access to enantiomers and isomeric forms.

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Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Synthetic Methodology

Background:

  • Epoxides are versatile synthetic intermediates.
  • Stereoselective synthesis is crucial in organic chemistry.
  • Controlling stereochemistry in epoxide ring-opening reactions is challenging.

Purpose of the Study:

  • To develop a new synthetic method for inverting the configurations of both epoxide carbons.
  • To demonstrate the utility of this method with relevant examples.

Main Methods:

  • A sequence of chemical reactions was designed and executed.
  • The method was applied to (+)-disparlure and a cyclohexene oxide derivative.

Main Results:

  • Complete inversion of both epoxide carbons was achieved.
  • (+)-disparlure was successfully converted to its enantiomer, (-)-disparlure.
  • An exo-endo conversion of a cyclohexene oxide was demonstrated.

Conclusions:

  • The presented reaction sequence is effective for inverting epoxide configurations.
  • This method offers a valuable tool for stereoselective synthesis.
  • The approach is applicable to various 1,2-disubstituted epoxides.