Related Experiment Video
Updated: Feb 2, 2026
05:51
Direct Detection of the Acetate-forming Activity of the Enzyme Acetate Kinase
Published on: December 19, 2011
23.7K
TiC14 promoted three component coupling reaction: an efficient method for the substituted tetrahydropyrilidene
Arun K Ghosh1, Reiko Kawahama1
1Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, Illinois 60607, USA.
Tetrahedron Letters
|November 24, 2018
Summary
Researchers developed a new method for synthesizing substituted tetrahydropyrilidene acetates using a three-component coupling reaction. This efficient process involves ethyl glyoxylate, 3,4-dihydro-2H-pyran, and various nucleophiles, with temperature influencing the product.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Tetrahydropyrilidene acetates are important organic compounds.
- Efficient synthesis methods are crucial for accessing diverse chemical structures.
Purpose of the Study:
- To develop a novel, efficient three-component coupling reaction for synthesizing substituted tetrahydropyrilidene acetates.
- To explore the use of titanium tetrachloride (TiCl4) as a promoter in this coupling reaction.
Main Methods:
- The synthesis involved a carbon-carbon bond-forming reaction.
- Key reactants included ethyl glyoxylate, 3,4-dihydro-2H-pyran, and a nucleophile (carbon, oxygen, or sulfur-based).
- Titanium tetrachloride (TiCl4) was used as a catalyst/promoter.
Main Results:
- An efficient three-component coupling process was established.
- Substituted tetrahydropyrilidene acetates were successfully synthesized.
- The olefinic coupling product formation was found to be dependent on the reaction temperature.
Conclusions:
- The developed method provides an efficient route to substituted tetrahydropyrilidene acetates.
- The reaction's outcome is tunable via temperature control.
- This approach offers a versatile strategy for constructing complex organic molecules.
Related Concept Videos
01:17Coupled Reactions
10.7K
Cellular processes such as building and breaking down complex molecules occur through stepwise chemical reactions. Some of these chemical reactions are spontaneous and release energy, whereas others require energy to proceed. Cells often couple the energy-releasing reaction with the energy-requiring one to carry out important cell functions.
Energy in adenosine triphosphate or ATP molecules is easily accessible to do work. ATP powers the majority of energy-requiring cellular reactions....
Energy in adenosine triphosphate or ATP molecules is easily accessible to do work. ATP powers the majority of energy-requiring cellular reactions....
10.7K
02:34Nucleophilic Substitution Reactions
19.5K
Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
19.5K
01:38Preparation of Alcohols via Substitution Reactions
7.4K
Overview
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
7.4K
01:08Vector Algebra: Method of Components
19.5K
It is cumbersome to find the magnitudes of vectors using the parallelogram rule or using the graphical method to perform mathematical operations like addition, subtraction, and multiplication. There are two ways to circumvent this algebraic complexity. One way is to draw the vectors to scale, as in navigation, and read approximate vector lengths and angles (directions) from the graphs. The other way is to use the method of components.
In many applications, the magnitudes and directions of...
In many applications, the magnitudes and directions of...
19.5K
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
2.5K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.5K
01:17Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution
3.9K
Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
3.9K