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

Conformations of Cycloalkanes

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3 hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.

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.

Conformations of Ethane and Propane

Conformations of Ethane and Propane

In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered...

α-Alkylation of Ketones via Enolate Ions

α-Alkylation of Ketones via Enolate Ions

Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...

You might also read

Related Articles

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

Sort by

Same author

A Safe Approach to meta-Fluorinated Pyridines.

Angewandte Chemie (International ed. in English)·2026

Same author

<i>O</i>-Vinylhydroxylamines for <i>De Novo</i> Pyrrole Synthesis.

Journal of the American Chemical Society·2026

Same author

Replacement of the Piperidine Ring with Aza-Spirocycles Reduces Cardiotoxicity of the Local Anesthetic Drug Bupivacaine.

Journal of medicinal chemistry·2026

Same author

Electrochemical functionalization of pyridines.

Chemical science·2026

Same author

Smallest Bicycles in Medicinal Chemistry: Where Are We Now?

Chemical reviews·2026

Same author

Mechanistically Guided Functionalization of α,α-Disubstituted Alkenyl Amides Enabled by a Conformationally Flexible Directing Auxiliary.

Journal of the American Chemical Society·2026

Search research articles

Related Experiment Video

Updated: Jan 8, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Ring-Expansion of Ketones with [1.1.1]Propellane.

Ganesh Arjun Kadam¹, Suparnak Midya¹, Vitalina Levchenko^2,3

¹Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.

Journal of the American Chemical Society

|December 22, 2025

Summary

This study introduces a new method for ketone ring-expansion using [1.1.1]propellane. The practical and scalable reaction efficiently produces valuable spirocyclic compounds for synthesis and drug discovery.

More Related Videos

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

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Related Experiment Videos

Last Updated: Jan 8, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

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

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Area of Science:

Organic Chemistry
Synthetic Methodology
Medicinal Chemistry

Background:

Spirocyclic scaffolds are crucial in drug discovery.
Efficient synthesis of complex spirocycles remains a challenge.

Purpose of the Study:

To develop a novel ring-expansion method for ketones.
To enable the synthesis of diverse spirocyclic structures.

Main Methods:

Electrophilic activation of [1.1.1]propellane.
Reaction with a broad spectrum of ketones.
Mechanistic studies using control experiments and DFT calculations.

Main Results:

Successful ring-expansion of various ketones.
Excellent functional group tolerance (esters, amides, amines).
Scalable synthesis demonstrated up to 56 g.
Preparation of mono-, bis-, and tris-spirocyclic scaffolds.

Conclusions:

The developed method is practical and scalable.
It provides access to valuable spirocyclic compounds.
Mechanistic understanding was achieved through experimental and computational studies.