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Related Concept Videos

Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

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The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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NMR Spectroscopy: Chemical Shift Overview01:15

NMR Spectroscopy: Chemical Shift Overview

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The position of the absorption signal of a sample is reported relative to the position of the signal of tetramethylsilane (TMS), which is added as an internal reference while recording spectra. The difference between the absorption frequencies of the sample and TMS (in Hz) is divided by the spectrometer operating frequency (in MHz) to obtain a dimensionless quantity called the chemical shift. It is reported on the δ (delta) scale and expressed in parts per million.
For instance, the proton...
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Proton (¹H) NMR: Chemical Shift01:07

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Organic molecules primarily contain carbon and hydrogen atoms. While all the hydrogen isotopes are NMR-active, protium or hydrogen-1 is the most abundant. It has a significant energy separation between its nuclear spin states due to its large gyromagnetic ratio. As per Boltzmann's distribution, an increase in the energy separation implies a greater excess population of nuclei available for excitation, resulting in a strong NMR absorption signal.
Absorption signals of all the protium nuclei...
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Chemical Shift: Internal References and Solvent Effects01:17

Chemical Shift: Internal References and Solvent Effects

1.3K
In an NMR sample, precise measurement of the absolute absorption frequencies of nuclei is difficult. A standard internal reference compound is added, and the frequency difference between the reference signal and sample signals is measured.
The internal reference compound generally used in NMR spectroscopy is tetramethylsilane (TMS). TMS is preferred because it is chemically inert, soluble in NMR solvents, and easily removable. Also, the highly shielded methyl protons in TMS yield an intense...
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π Electron Effects on Chemical Shift: Overview01:27

π Electron Effects on Chemical Shift: Overview

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An applied magnetic field causes loosely bound π-electrons in organic molecules to circulate, producing a local or induced diamagnetic field over a large spatial volume. As the molecules tumble in solution, the field generated by π-electrons in spherical substituents results in a zero net field. However, the net field generated by π-electrons in non-spherical substituents is not zero. The effect of this induced field depends on the orientation of the molecule with respect to B0,...
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Spirocyclic Tetramates by Sequential Knoevenagel and [1,5]-Prototropic Shift.

Laia Josa-Culleré1, Michael G Hirst1, Jonathan P Lockett1

  • 1Chemistry Research Laboratory , University of Oxford , Mansfield Road , Oxford OX1 3TA , U.K.

The Journal of Organic Chemistry
|July 6, 2019
PubMed
Summary

Researchers synthesized novel spirocyclic tetramates using a Knoevenagel reaction and T-reaction. Stable analogues were developed, offering potential scaffolds for medicinal chemistry applications.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry

Background:

  • Spirocyclic tetramates are versatile heterocyclic compounds.
  • Developing efficient synthetic routes to functionalized tetramates is crucial for exploring their chemical space.

Purpose of the Study:

  • To develop a novel synthetic strategy for highly functionalized spirocyclic tetramates.
  • To investigate the stability and potential applications of these novel compounds.

Main Methods:

  • Sequential Knoevenagel reaction and [1,5]-prototropic shift (T-reaction) of bicyclic tetramates.
  • Systematic variation of substituents to achieve stable analogues.
  • Introduction of aromatic groups for further derivatization.

Main Results:

  • Successful synthesis of highly functionalized spirocyclic tetramates.
  • Identification of conditions for preparing stable tetramate analogues.
  • Demonstration of the feasibility of introducing aromatic moieties.

Conclusions:

  • The developed synthetic route provides access to novel spirocyclic tetramates.
  • Stable analogues can be accessed, expanding their utility.
  • These compounds serve as promising skeletons for medicinal chemistry exploration.