Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
C–C Bond Cleavage: Retro-Aldol Reaction00:57

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.

You might also read

Related Articles

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

Sort by
Same author

Sonodynamic therapy inhibits angiogenesis and tumor growth in a xenograft mouse model.

Cancer letters·2013
Same author

[Study on effect of coptidis rhizoma on red blood cells of normal mice and its antioxidant property].

Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica·2013
Same author

General framework to histogram-shifting-based reversible data hiding.

IEEE transactions on image processing : a publication of the IEEE Signal Processing Society·2013
Same author

The prevalences of Neisseria gonorrhoeae and Chlamydia trachomatis infections among female sex workers in China.

BMC public health·2013
Same author

[Study on allocation rules of common nutrients in Scutellaria baicalensis in different phenological periods by ICP-OES].

Guang pu xue yu guang pu fen xi = Guang pu·2013
Same author

Sesterterpenoids.

Natural product reports·2013
Same journal

Total Synthesis and Structural Revision of Tetracyclic Diterpenoid (±)-Papililone A and (-)-Papililone A.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same journal

Light-Powered Atroposelective Ratcheting via Excited-State Donor-Acceptor Interactions.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same journal

Modular One-Pot Access to π-Expanded Tetrakis(Phenothiazinyl)-Silanes With Broadly Tunable Redox and Emission Properties.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same journal

pH-Tolerant Tripeptide Coacervates as Biomimetic Catalytic Microreactors.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same journal

Nano-Nickel Pinned Defective MoS<sub>2</sub> Heterostructures via Ball Milling for Improved Hydrogen Evolution.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same journal

Hollow NiCo-LDH Nanocage Derived From ZIF-67 as an Efficient Catalyst for the Thermal Decomposition of Ammonium Perchlorate.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
See all related articles

Related Experiment Video

Updated: Jun 2, 2026

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Copper-catalyzed C-P coupling through decarboxylation

Jie Hu1, Ning Zhao, Bin Yang

  • 1State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 16, 2011
PubMed
Summary

No abstract available in PubMed .

More Related Videos

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Related Experiment Videos

Last Updated: Jun 2, 2026

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022