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Related Concept Videos

Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.

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Related Experiment Video

Updated: May 26, 2026

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Reductive heterocoupling mediated by Cp*2U(2,2'-bpy).

Adil Mohammad1, Dennis P Cladis, William P Forrest

  • 1H.C. Brown Laboratory, Department of Chemistry, Purdue University, West Lafayette, IN 47907, USA.

Chemical Communications (Cambridge, England)
|December 22, 2011
PubMed
Summary
This summary is machine-generated.

Uranium complexes with a monoanionic bipyridine ligand were reacted with aldehydes and ketones. This reaction yielded new uranium(IV) derivatives through carbonyl reduction and radical coupling.

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

Area of Science:

  • Organometallic Chemistry
  • Uranium Chemistry
  • Coordination Chemistry

Background:

  • Trivalent uranium complexes featuring cyclopentadienyl and bipyridine ligands are valuable synthetic intermediates.
  • The reactivity of the carbonyl group in aldehydes and ketones presents opportunities for novel ligand functionalization.

Purpose of the Study:

  • To explore the reaction of a trivalent uranium complex, Cp*(2)U(2,2'-bpy)(2), with various carbonyl compounds.
  • To synthesize and characterize novel uranium(IV) derivatives resulting from carbonyl reduction and radical coupling.

Main Methods:

  • Treatment of the trivalent uranium precursor with p-tolualdehyde, furfuraldehyde, acetone, and benzophenone.
  • Characterization of the resulting uranium(IV) products using spectroscopic and analytical techniques.

Main Results:

  • Successful synthesis of four new uranium(IV) complexes, denoted as [Cp*(2)U(2,2'-bpy)(OCRR')](3a-d).
  • The reaction mechanism involves the reduction of the carbonyl C=O bond followed by radical coupling with the bipyridine ligand.

Conclusions:

  • Demonstrated a novel synthetic route to uranium(IV) complexes via carbonyl functionalization.
  • The study expands the known reactivity of trivalent uranium complexes and provides access to new organouranium compounds.