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

Reactions at the Benzylic Position: Oxidation and Reduction

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.

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...

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Oxymercuration-Reduction of Alkenes

Oxymercuration-Reduction of Alkenes

Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...

You might also read

Related Articles

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

Sort by

Same author

Oxetane-to-azetidine skeletal editing.

Nature chemistry·2026

Same author

Engineering Silk Fibroin-Based Biomaterials for Neural Repair.

Advanced materials (Deerfield Beach, Fla.)·2026

Same author

Transition-metal-free electrochemical cross-electrophile coupling of activated benzyl alcohols and primary alkyl bromides.

Science advances·2026

Same author

Biomimetic Multichannel Silk Nerve Conduits With Multicellular Spatiotemporal Distributions for Spinal Cord Injury Repair.

Advanced materials (Deerfield Beach, Fla.)·2024

Same author

Engineered photoresponsive biohybrids for tumor therapy.

Smart medicine·2024

Same author

Bioceramic materials with ion-mediated multifunctionality for wound healing.

Smart medicine·2024

Search research articles

Related Experiment Video

Updated: Jun 23, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Modular Access to Functionalized Oxetanes as Benzoyl Bioisosteres.

Dayu Tian¹, Guang Chen¹, Xiaocheng Wang¹

¹Key Laboratory of Precision and Intelligent Chemistry, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China.

Journal of the American Chemical Society

|June 21, 2024

Summary

Synthesizing functionalized 3-aryl oxetanes, valuable drug discovery bioisosteres, is now accessible. A novel modular strategy using oxetanyl trichloroacetimidates overcomes previous synthetic hurdles for drug and agrochemical development.

More Related Videos

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Related Experiment Videos

Last Updated: Jun 23, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Area of Science:

Medicinal Chemistry
Organic Synthesis
Agrochemical Research

Background:

Bioisosterism is key for optimizing drug properties.
3-Aryl oxetanes are important benzoyl bioisosteres but synthetically challenging.
Limited use in pharmaceuticals and agrochemicals due to synthetic difficulties.

Purpose of the Study:

To develop a modular synthetic strategy for functionalized 3-aryl oxetanes.
To enable easier access to oxetane analogues for drug discovery and agrochemical applications.
To overcome the synthetic challenges associated with 3-aryl oxetanes.

Main Methods:

A novel modular synthesis using oxetanyl trichloroacetimidates.
Strategy inspired by Schmidt glycosylation, utilizing aryl halides and nucleophiles.
Application in late-stage functionalization and analogue synthesis.

Main Results:

Developed an operationally simple protocol for diverse functionalized oxetanes.
Demonstrated broad applicability through late-stage functionalization of complex molecules.
Enabled rapid synthesis of oxetane analogues of known bioactive compounds and marketed drugs.

Conclusions:

The new strategy provides facile access to valuable 3-aryl oxetanes.
This approach facilitates the exploration of oxetanes in drug discovery and agrochemicals.
Mechanistic insights suggest the oxetane oxygen stabilizes key carbocation intermediates.