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¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.0K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
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Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

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Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...
1.2K
Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)

1.2K
Vicinal or three-bond coupling is commonly observed between protons attached to adjacent carbons. Here, nuclear spin information is primarily transferred via electron spin interactions between adjacent C‑H bond orbitals. This generally favors the antiparallel arrangement of spins, so 3J values are usually positive.
The extent of coupling depends on the C‑C bond length, the two H‑C‑C angles, any electron-withdrawing substituents, and the dihedral angle between the...
1.2K
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

1.1K
Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...
1.1K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.9K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.9K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.9K

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Cross-dehydrogenative N-N couplings.

Alexis Tabey1, Pooja Y Vemuri1, Frederic W Patureau1

  • 1Institute of Organic Chemistry, RWTH Aachen University Landoltweg 1 52074 Aachen Germany Frederic.Patureau@rwth-aachen.de.

Chemical Science
|December 9, 2021
PubMed
Summary

Forming nitrogen-nitrogen bonds via cross-coupling is challenging due to nitrogen

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Nitrogen-nitrogen (N-N) bonds are crucial in organic chemistry, yet their formation via cross-coupling reactions is hindered by nitrogen's high electronegativity.
  • Intermolecular N-N bond formation, particularly through dehydrogenative coupling, presents significant synthetic challenges.
  • Dehydrogenative couplings offer step and atom economy but require careful oxidant selection to avoid side reactions like homocoupling or C-N/C-C coupling.

Purpose of the Study:

  • To review and analyze the limited existing examples of intermolecular hetero N-N cross-dehydrogenative coupling reactions.
  • To provide insights into the difficulties and strategies associated with forming N-N bonds under these conditions.
  • To offer a perspective on future research directions for advancing N-N bond formation methodologies.

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Main Methods:

  • Literature review and analysis of reported intermolecular hetero N-N cross-dehydrogenative coupling reactions.
  • Examination of reaction mechanisms, catalyst systems, and oxidant choices in the studied examples.
  • Comparative analysis of successful and unsuccessful coupling strategies.

Main Results:

  • Identified a scarcity of efficient intermolecular hetero N-N cross-dehydrogenative coupling reactions.
  • Highlighted the critical role of oxidant selection in achieving selective N-N bond formation.
  • Demonstrated the challenges in preventing competing homocoupling and cross-coupling pathways.

Conclusions:

  • Intermolecular N-N cross-dehydrogenative coupling remains a difficult but important synthetic transformation.
  • Further development requires innovative strategies for oxidant activation and selectivity control.
  • This review sets the stage for future research to overcome current limitations in N-N bond synthesis.