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Nitrosation of Enols01:19

Nitrosation of Enols

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The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
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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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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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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...
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α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

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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...
3.0K
Preparation of Nitriles01:12

Preparation of Nitriles

2.0K
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...
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Oxidative Nitrogen Insertion into Silyl Enol Ether C═C Bonds.

Alex Lin1, Arghya Ghosh1, Simon Yellen1

  • 1Department of Chemistry, Rice University, Houston, Texas 77005, United States.

Journal of the American Chemical Society
|July 16, 2024
PubMed
Summary

Researchers discovered a new way to insert nitrogen into molecules using silyl enol ethers and an iodonitrene-like species. This method creates valuable alpha-amido alkylating agents for complex molecule synthesis and late-stage functionalization.

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Reaction Discovery

Background:

  • Silyl enol ethers are versatile nucleophilic building blocks in organic synthesis.
  • Developing novel methods for nitrogen insertion into organic frameworks remains a key challenge.
  • Existing methods often lack regioselectivity or require harsh conditions.

Purpose of the Study:

  • To introduce a novel reactivity of silyl enol ethers involving nitrogen atom insertion.
  • To develop a facile and efficient method for synthesizing alpha-amido alkylating agents.
  • To enable late-stage functionalization and modification of complex organic molecules.

Main Methods:

  • Utilizing an in situ-generated iodonitrene-like species to react with silyl enol ethers.
  • Investigating the mechanism of nitrogen insertion and C=C bond cleavage.
  • Correlating reaction efficiency with the nucleophilicity of silyl enol ethers using the Mayr N scale.

Main Results:

  • A new transformation that inserts a nitrogen atom between the olefinic carbons of silyl enol ethers.
  • Conversion of C-nucleophilic silyl enol ethers to C-electrophilic N-acyl-N,O-acetals.
  • Demonstrated modular derivatization of the resulting acetals with various nucleophiles.
  • Successful late-stage nitrogen insertion into natural product skeletons with high regioselectivity.

Conclusions:

  • This work presents an unprecedented method for accessing alpha-amido alkylating agents.
  • The developed methodology offers a powerful tool for late-stage carbon framework editing.
  • The reaction is efficient and its scope is predictable based on enol ether nucleophilicity.
  • Applications include selective 15N labeling of amides and lactams.