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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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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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Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
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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...
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In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
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Acid-Catalyzed Ring-Opening of Epoxides02:24

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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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When a carbonyl compound is treated with a strong base, the α position gets deprotonated to give a resonance-stabilized intermediate called an enolate. Enolates are ambident nucleophiles because they possess two nucleophilic sites that can attack an electrophile owing to the delocalization of the negative charge between the α carbon and oxygen atoms. When the oxygen atom attacks an electrophile, it is called O-attack, whereas electrophilic attack via the α carbon is known as...
2.3K
Hydroboration-Oxidation of Alkenes03:08

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Transition structures for the oxy-ene reaction.

Shengwen Yang1,2, Solène Miaskiewicz1, Christophe Bour1

  • 1Université Paris-Saclay, CNRS, Institut de Chimie Moléculaire et des Matériaux d'Orsay, 91405, Orsay, France. vincent.gandon@universite-paris-saclay.fr.

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Researchers analyzed a novel oxy-ene reaction between allyl alcohols and alkenes. This pericyclic reaction forms carbonyl compounds and may play a role in natural biosynthetic pathways.

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Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms

Background:

  • Pericyclic reactions are crucial in organic synthesis.
  • The Alder-ene reaction and oxy-Cope rearrangement are well-established transformations.
  • A specific reaction between allyl alcohols and alkenes has been overlooked.

Purpose of the Study:

  • To analyze an overlooked pericyclic reaction between allyl alcohols and alkenes.
  • To understand the mechanistic link between Alder-ene and oxy-Cope reactions.
  • To explore the potential role of this reaction in biosynthesis.

Main Methods:

  • Theoretical analysis of the reaction mechanism.
  • Computational chemistry studies.
  • Comparison with known pericyclic reactions.

Main Results:

  • Identification and characterization of a novel oxy-ene reaction.
  • The reaction proceeds through a concerted pericyclic pathway.
  • The reaction mechanism shares features with both Alder-ene and oxy-Cope reactions.

Conclusions:

  • The oxy-ene reaction represents a new synthetic route to carbonyl compounds.
  • This reaction expands the scope of known pericyclic transformations.
  • The identified reaction mechanism suggests potential involvement in natural product biosynthesis.