Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Protection of Alcohols

Protection of Alcohols

This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...

Protecting Groups for Aldehydes and Ketones: Introduction

Protecting Groups for Aldehydes and Ketones: Introduction

Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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.

Photochemical Electrocyclic Reactions: Stereochemistry

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

Preparation of Epoxides

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

C1'-Substituted Penta- and Heptamethine Cyanines: Synthetic Scope and Properties.

The Journal of organic chemistry·2026

Same author

How Much Chirality is Enough?

Chimia·2026

Same author

π-Radical Cascades to Peri-Fused Triangulene Dimers.

Angewandte Chemie (International ed. in English)·2026

Same author

Experimental Study Redefines the Mechanism of Heptamethine Cyanine Phototruncation.

Journal of the American Chemical Society·2026

Same author

Incidence of adverse events in iron-deficient pregnant women and surgical patients undergoing intravenous iron treatment with ferric isomaltose or ferric carboxymaltose: A systematic review.

Transfusion·2026

Same author

Acidity changes in glycine and L-histidine buffers, mannitol, and their mixtures after freezing and lyophilization.

International journal of pharmaceutics·2026

Search research articles

Related Experiment Video

Updated: May 20, 2026

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Published on: October 15, 2019

2-Hydroxyphenacyl ester: a new photoremovable protecting group.

Bokolombe Pitchou Ngoy¹, Peter Sebej, Tomáš Solomek

¹Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00, Brno, Czech Republic.

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology

|July 7, 2012

Summary

A novel 2-hydroxyphenacyl group offers efficient photoremovable protection for carboxylates and sulfonates. This new protecting group is released via a short-lived triplet state, confirmed by laser flash photolysis and quantum chemical calculations.

More Related Videos

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Related Experiment Videos

Last Updated: May 20, 2026

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds

Published on: October 15, 2019

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Area of Science:

Organic Chemistry
Photochemistry
Computational Chemistry

Background:

Photoremovable protecting groups are crucial tools in organic synthesis.
Development of new photoremovable protecting groups with tailored absorption properties is an ongoing area of research.
Carboxylates and sulfonates are common functional groups requiring protection during synthetic transformations.

Purpose of the Study:

To introduce and characterize a novel 2-hydroxyphenacyl moiety as a photoremovable protecting group.
To investigate the photophysical and photochemical properties governing the release mechanism.
To elucidate the key reaction pathways involved in the photodeprotection process using computational methods.

Main Methods:

Laser flash photolysis and steady-state sensitization studies were employed to probe the excited state dynamics.
Density Functional Theory (DFT)-based quantum chemical calculations were performed to model reaction mechanisms.
Spectroscopic techniques were utilized to characterize intermediates and reaction products.

Main Results:

The 2-hydroxyphenacyl moiety effectively functions as a photoremovable protecting group for carboxylates and sulfonates, absorbing light below 370 nm.
Photodeprotection occurs via a short-lived triplet excited state.
Triplet excited state intramolecular proton transfer was identified as a major deactivation pathway, alongside minor productive pathways involving triplet anion and quinoid triplet enol intermediates.

Conclusions:

The 2-hydroxyphenacyl group represents a promising new photoremovable protecting group with efficient cleavage mechanisms.
Understanding the excited state dynamics, particularly the role of intramolecular proton transfer, is key to optimizing its application.
This work provides valuable insights for the design of next-generation photolabile protecting groups.