Related Experiment Video
Updated: Jul 11, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Stereoselective preparation of dienyl zirconocene complexes via a tandem allylic C-H bond activation-elimination
Nicka Chinkov1, Swapan Majumdar, Ilan Marek
1Department of Chemistry and Institute of Catalysis Science and Technology, Technion-Israel Institute of Technology, Technion City, 32000 Haifa, Israel. chilanm@tx.technion.ac.il
Abstract:
Several dienyl zirconocene derivatives were easily prepared, as unique geometrical isomers, from simple non-conjugated unsaturated enol ethers with (1-butene)ZrCp2 complexes. This new methodology is based on a tandem allylic C-H bond activation-elimination sequence and the mechanism has been mapped out by deuterium labeling experiments. The stereochemical outcome of this process was determined by addition of several electrophiles. Moreover, when the organometallic derivative is vinylic as well as allylic such as in 44-47Zr, an unexpected reversal of the stereochemistry has been found during the zirconium to copper transmetalation step.
Related Concept Videos
Elimination Reactions
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Amines to Alkenes: Cope Elimination
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
Radical Formation: Elimination

