Related Experiment Video
Updated: Jan 24, 2026
06:00
One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
Published on: January 15, 2018
7.9K
Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles
Nivedita S Mahajani1, Rowan I L Meador1, Tomas J Smith1
1Department of Chemistry , Syracuse University , 1-014 Center for Science and Technology , Syracuse , New York 13244 , United States.
The Journal of Organic Chemistry
|May 24, 2019
Summary
Trichloroacetimidates offer mild and promoter-free ester synthesis, preserving sensitive functional groups. This method efficiently forms esters, even in complex molecules, with potential for benzyl ester synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Ester synthesis often requires harsh conditions (strong acids) that can degrade sensitive molecules.
- Trichloroacetimidates are known reagents for esterification.
Purpose of the Study:
- To explore the utility of trichloroacetimidates for mild ester synthesis.
- To demonstrate the avoidance of sensitive functional group decomposition.
- To extend the method to benzyl ester synthesis.
Main Methods:
- Utilizing trichloroacetimidates as reagents for ester formation.
- Performing reactions under mild conditions without exogenous promoters.
- Applying heat to facilitate reactions with specific substrates like benzyl esters.
Main Results:
- Ester synthesis was achieved under mild conditions, avoiding decomposition of sensitive substrates.
- The method successfully synthesized benzyl esters, including those lacking electron-donating groups.
- The reactions were found to be inexpensive and convenient.
Conclusions:
- Trichloroacetimidates provide a mild and effective route for ester synthesis.
- This method is suitable for substrates with sensitive functional groups.
- The approach is valuable for synthesizing esters in complex molecules.
Related Concept Videos
02:28Electrophiles
12.7K
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
12.7K
01:02Radical Reactivity: Electrophilic Radicals
2.4K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
2.4K
02:35Regioselectivity of Electrophilic Additions-Peroxide Effect
10.4K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
10.4K
01:16Electrophilic Aromatic Substitution: Overview
13.6K
In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
13.6K
02:38Electrophilic Addition to Alkynes: Halogenation
10.0K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
10.0K
02:35Electrophilic Addition to Alkynes: Hydrohalogenation
11.4K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
11.4K