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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
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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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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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.
2.9K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.5K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.5K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.1K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
4.1K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.1K
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
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

7.3K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
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Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics.

Mark A R de Geus1, Elmer Maurits1, Alexi J C Sarris1

  • 1Leiden Institute of Chemistry and The Institute for Chemical Immunology, Leiden University, Einsteinweg 55, 2333 CC, Leiden, The Netherlands.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 11, 2020
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Summary

Researchers developed a new fluorogenic tool to accurately measure the speed of bioorthogonal bond cleavage reactions. This method precisely determines reaction rates for tetrazines and trans-cyclooctenes (TCOs) at physiological conditions.

Keywords:
Diels-Alder reactionsbioorthogonal chemistryfluorescent probeskineticsnitrogen heterocycles

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Area of Science:

  • Bioorthogonal chemistry
  • Chemical biology
  • Reaction kinetics

Background:

  • Inverse electron demand Diels-Alder (IEDDA) reactions involving tetrazines and trans-cyclooctenes (TCOs) are crucial for bioorthogonal bond cleavage.
  • Accurate determination of elimination kinetics for alkylamine substrates in these reactions remains challenging.

Purpose of the Study:

  • To develop a novel fluorogenic tool for precise measurement of tetrazine-TCO click and release rate constants.
  • To enable kinetic studies of bioorthogonal reactions at physiologically relevant concentrations.

Main Methods:

  • Utilized a fluorogenic probe comprising a TCO-linked EDANS fluorophore and a DABCYL quencher.
  • Applied the probe to quantify click and release rate constants for various tetrazines.
  • Performed measurements at physiologically relevant concentrations.

Main Results:

  • Successfully developed a sensitive fluorogenic tool for kinetic analysis of IEDDA reactions.
  • Demonstrated accurate determination of both click and release rate constants.
  • Validated the method's utility across different tetrazine substrates.

Conclusions:

  • The developed fluorogenic probe provides a robust method for studying tetrazine-based bioorthogonal reactions.
  • This tool facilitates precise kinetic characterization, aiding in the design and application of bioorthogonal chemistry.