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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 acids to...
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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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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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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...
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Reactions at the Benzylic Position: Oxidation and Reduction00:59

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The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
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α-Alkylation of Ketones via Enolate Ions01:10

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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Benzylic Ammonium Ylide Mediated Epoxidations.

Lukas Roiser1, Raphaël Robiette2, Mario Waser1

  • 1Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, Austria.

Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry
|October 22, 2016
PubMed
Summary

A new method for synthesizing stilbene oxides with high yields was developed using ammonium ylides. The choice of amine leaving group significantly impacts reaction outcomes and diastereoselectivity.

Keywords:
DFT calculationsdiastereoselectivitydiazo compoundsepoxidesylides

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Stilbene oxides are important intermediates in organic synthesis.
  • Developing efficient and selective synthetic routes is crucial.

Purpose of the Study:

  • To develop a high-yielding synthesis of stilbene oxides.
  • To investigate the role of the amine leaving group in ammonium ylide reactions.
  • To understand the factors influencing diastereoselectivity.

Main Methods:

  • Synthesis of stilbene oxides using ammonium ylides.
  • Varying the amine leaving group (trimethylamine, DABCO, quinuclidine).
  • Detailed Density Functional Theory (DFT) calculations.

Main Results:

  • A high-yielding synthetic route was established.
  • Trimethylamine as a leaving group provided superior yields compared to DABCO and quinuclidine.
  • The amine group was found to influence diastereoselectivity.

Conclusions:

  • Ammonium ylide-mediated synthesis offers an efficient pathway to stilbene oxides.
  • The amine leaving group is a critical determinant of yield and stereochemical outcome.
  • DFT calculations provide insights into reaction mechanisms and selectivity.