Related Experiment Video
Updated: Jun 11, 2025
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Water as a Reactant: DABCO-Catalyzed Hydration of Activated Alkynes for the Synthesis of Divinyl Ethers
Raquel Diana-Rivero1, David S Rivero1, Alba García-Martín1
1Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas, Avda. Astrofísico Francisco Sánchez 3, 38 206 La Laguna, Tenerife, Islas Canarias, Spain.
Abstract:
A practical and efficient addition of water to readily available activated alkynes delivering divinyl ethers is reported. The reaction proceeds with full atom economy in a very straightforward experimental procedure. Additionally, of all the tertiary amines studied to catalyze the reaction, the best and most efficient is clearly DABCO (1,4-diazabicyclo[2.2.2]octane). Finally, the solvent choice is crucial for the efficiency of this process and we have found that the reaction is best performed in wet dichloromethane for propiolic esters and alkynones, and in wet acetonitrile for propiolamides.
More Related Videos
05:34Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
10:12Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Related Concept Videos
02:40Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
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.
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
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.
01:20Aldehydes and Ketones with Water: Hydrate Formation
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
02:35Acid-Catalyzed Dehydration of Alcohols to Alkenes
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
02:45Acid-Catalyzed Hydration of Alkenes