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C–C Bond Cleavage: Retro-Aldol Reaction

C–C Bond Cleavage: Retro-Aldol Reaction

The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.

Radical Formation: Homolysis

Radical Formation: Homolysis

A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.

Bond Dissociation Energy and Activation Energy

Bond Dissociation Energy and Activation Energy

Bond energy is the energy required to break a bond homolytically. These values are usually expressed in units of kcal/mol or kJ/mol and are referred to as bond dissociation energies when given for specific bonds or average bond energies when indicated for a given type of bond over many compounds. Firstly, the bond dissociation energy for a single bond is weaker than that of a double bond, which in turn is weaker than that of a triple bond. Secondly, hydrogen forms relatively strong bonds with...

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...

Cycloaddition Reactions: MO Requirements for Thermal Activation

Cycloaddition Reactions: MO Requirements for Thermal Activation

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.

Radical Formation: Overview

Radical Formation: Overview

A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...

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Related Experiment Video

Updated: Jun 16, 2025

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Click-Triggered Bioorthogonal Bond-Cleavage Reactions.

Patrick Keppel¹, Sebastian Hecko¹, Hannes Mikula²

¹Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060, Vienna, Austria.

Topics in Current Chemistry (Cham)

|June 14, 2025

Summary

Bioorthogonal bond-cleavage reactions enable controlled molecular release in living systems. This review details click-triggered chemistries for enhanced bioorthogonal applications.

Keywords:

Bioorthogonal chemistry Click chemistry Click-to-release Cycloaddition Elimination

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Last Updated: Jun 16, 2025

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Published on: August 19, 2012

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Published on: February 7, 2021

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Microfluidic On-chip Capture-cycloaddition Reaction to Reversibly Immobilize Small Molecules or Multi-component Structures for Biosensor Applications

Published on: September 23, 2013

Area of Science:

Chemical biology
Molecular imaging
Drug delivery

Background:

Bioorthogonal reactions facilitate precise chemical modifications within biological environments.
Controlled molecular release is crucial for targeted therapies and diagnostics.
Existing bioorthogonal tools require optimization for in vivo applications.

Purpose of the Study:

To provide a concise overview of click-triggered bioorthogonal bond-cleavage reactions.
To emphasize the mechanisms and characteristics of common click-to-release chemistries.
To highlight advancements in bioorthogonal tool development.

Main Methods:

Literature review of bioorthogonal bond-cleavage reactions.
Analysis of click-to-release mechanisms.
Comparison of different bioorthogonal chemistries based on performance and biocompatibility.

Main Results:

Identification of key bioorthogonal bond-cleavage strategies.
Characterization of reaction kinetics and efficiency for various click-to-release systems.
Evaluation of biocompatibility and stability of commonly used bioorthogonal tools.

Conclusions:

Click-triggered bioorthogonal reactions are versatile tools for controlled molecular release.
Understanding reaction mechanisms is vital for optimizing bioorthogonal applications.
Continued development is needed to enhance performance and biocompatibility for in vivo use.