Related Experiment Video
Updated: Jul 3, 2026

Optimized Griess Reaction for UV-Vis and Naked-eye Determination of Anti-malarial Primaquine
Published on: October 11, 2019
The azaquinone-methide elimination: comparison study of 1,6- and 1,4-eliminations under physiological conditions
1Department of Organic Chemistry, School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel-Aviv University, Tel Aviv, Israel.
Abstract:
The azaquinone-methide elimination is a powerful and efficient reaction useful for disassembly of spacers in prodrug systems. We and others have used the spacer-technique to develop dendritic and polymeric self-immolative molecular systems that can disassemble through a domino-like mechanism upon a stimulus event. In this report, we study the disassembly of a system that can disintegrate through para- and ortho-azaquinone-methide eliminations. The disassembly was evaluated with molecules that undergo single 1,6- or 1,4-elimination and with molecules that undergo double 1,6- and 1,4-elimination. The 1,6-elimination was slightly faster than the 1,4-elimination under physiological conditions. This study sheds light on the disassembly-behavior of prodrug systems.
Related Concept Videos
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Amines to Alkenes: Hofmann Elimination
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
E2 Reaction: Stereochemistry and Regiochemistry
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major product and...
Pharmacokinetic–Pharmacodynamic Relationship: Influence of Elimination Half-Life on Effect Duration
Elimination Kinetics: First-Order and Zero-Order
Drug clearance depends on the rate of drug elimination and its plasma concentration. Another important parameter is a drug's half-life, which is the time required for its concentration to decrease by half. In most cases, drug clearance follows first-order kinetics,...
E1 Reaction: Stereochemistry and Regiochemistry

