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Related Concept Videos

Radical Formation: Elimination00:51

Radical Formation: Elimination

Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect to...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
Amines to Alkenes: Cope Elimination01:14

Amines to Alkenes: Cope Elimination

Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
Elimination Reactions02:25

Elimination Reactions

A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the elimination product by deprotonation of the neighboring carbon to form an alkene. In an elimination reaction, the substrate loses two groups from adjacent carbons forming at least one π bond. The carbon attached to the halogen is called the α carbon, while the adjacent carbon is called the β carbon; hence, these reactions are called β elimination or...
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...

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Related Experiment Video

Updated: Jun 18, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
09:45

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Published on: April 27, 2017

The pyridinone-methide elimination.

Rotem Perry-Feigenbaum1, Phil S Baran, Doron Shabat

  • 1Department of Organic Chemistry, School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel-Aviv University, Tel Aviv 69978, Israel.

Organic & Biomolecular Chemistry
|November 13, 2009
PubMed
Summary
This summary is machine-generated.

Researchers developed a novel pyridine-based self-immolative linker, demonstrating faster fragmentation and improved aqueous solubility compared to benzene systems. This pyridinone-methide elimination offers a new tool for drug delivery in aqueous environments.

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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

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Last Updated: Jun 18, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
09:45

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Published on: April 27, 2017

Facile Preparation of 4-Substituted Quinazoline Derivatives
11:51

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
06:18

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Biochemistry

Background:

  • Quinone-methide elimination is a key reaction for self-immolative linkers.
  • Developing efficient and tunable self-immolative systems is crucial for targeted drug delivery.

Purpose of the Study:

  • To investigate quinone-methide elimination within a pyridine ring system for the first time.
  • To compare the performance of pyridine-based self-immolative linkers with their benzene counterparts.
  • To explore the potential of pyridinone-methide elimination in aqueous environments.

Main Methods:

  • Synthesis of pyridine and benzene core-containing compounds with reporter molecules and enzymatic triggers.
  • Evaluation of 1,4-elimination reaction rates under physiological conditions.
  • Assessment of AB(2) self-immolative dendrons utilizing pyridinone-methide elimination.
  • Measurement of aqueous solubility for pyridine and benzene-based compounds.

Main Results:

  • Pyridine-based compounds exhibited significantly faster 1,4-elimination than benzene analogs under physiological conditions.
  • An AB(2) dendron based on a pyridine core demonstrated efficient release of two reporter units via 1,6- and 1,4-pyridinone-methide elimination.
  • Pyridine-based systems showed enhanced aqueous solubility compared to benzene-based systems.
  • The pyridinone-methide elimination reactions were faster in the pyridine system than the benzene system.

Conclusions:

  • The study successfully demonstrates quinone-methide elimination in a pyridine ring system.
  • Pyridine-based self-immolative linkers offer advantages in reaction kinetics and aqueous solubility over benzene analogs.
  • Pyridinone-methide elimination presents a promising alternative for designing self-immolative linkers for drug release in aqueous environments.