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Related Concept Videos

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
Types of Enols and Enolates01:19

Types of Enols and Enolates

Aldehydes and ketones form enols, although only about 1% of the enol is present at the equilibrium for simple monocarbonyl compounds. The enol form is undetectable for acetaldehyde, present as only 1.5 × 10−4 % of acetone, and present as only 1.2% of cyclohexanone. Two kinds of regioisomeric enols are possible for unsymmetrical ketones, and their net composition is 1% at equilibrium. This instability is due to the lower bond energy of C=C than the C=O group. The additional instability of enols...
Reactivity of Enols01:18

Reactivity of Enols

Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is governed by factors like...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.
Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

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 is more in the ring having a smaller number of...

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Published on: February 6, 2019

Stable acyclic aliphatic solid enols: synthesis, characterization, X-ray structure analysis and calculations.

Yu-Qiang Zhou1, Nai-Xing Wang, Yalan Xing

  • 1Technical Institute of Physics and Chemistry, Chinese Academy of Sciences , Beijing, 100190, China.

Scientific Reports
|January 16, 2013
PubMed
Summary

Researchers developed a new method to synthesize stable enols, creating solid acyclic aliphatic enols efficiently. These compounds were characterized, and their stability was analyzed using computational methods and various spectroscopic techniques.

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Published on: June 21, 2017

Area of Science:

  • Organic Chemistry
  • Physical Chemistry
  • Computational Chemistry

Background:

  • Enols are typically unstable and reactive intermediates.
  • The synthesis of stable enol forms, particularly acyclic aliphatic ones, presents a significant challenge in organic chemistry.

Purpose of the Study:

  • To introduce a novel synthetic approach for generating stable enols.
  • To synthesize and characterize a series of acyclic aliphatic solid enols.
  • To investigate the structure-stability relationship of these synthesized enols.

Main Methods:

  • Synthesis of acyclic aliphatic enols.
  • Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy ((1)H and (13)C), Mass Spectrometry (MS), and Infrared (IR) spectroscopy.
  • Structural confirmation partly through single-crystal X-ray diffraction and proton exchange experiments.
  • Computational analysis using Gaussian 09 calculations to rationalize enol stability.

Main Results:

  • A series of stable acyclic aliphatic solid enols were successfully synthesized.
  • The structures of the synthesized enols were confirmed by multiple spectroscopic and analytical techniques.
  • A correlation between molecular structure and enol stability was established and supported by computational data.

Conclusions:

  • A practical and efficient synthetic route to highly stable acyclic aliphatic enols has been developed.
  • These stable enols can be synthesized without the need for purification.
  • The study provides valuable insights into the factors governing enol stability.