Related Experiment Video
Updated: Jul 8, 2026

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
Published on: January 30, 2015
Metal vinylidenes as catalytic species in organic reactions
Barry M Trost1, Andrew McClory
1Department of Chemistry, Stanford University, Stanford, CA 94305, USA. bmtrost@stanford.edu
Abstract:
Organic vinylidene species have found limited use in organic synthesis owing to their inaccessibility. In contrast, metal vinylidenes are much more stable and may be readily accessed through transition-metal activation of terminal alkynes. These electrophilic species may be trapped by a number of nucleophiles. Additionally, metal vinylidenes can participate in pericyclic reactions and processes that involve migration of a metal ligand to the vinylidene species. This Focus Review addresses the reactions and applications of metal vinylidenes in organic synthesis.
Related Concept Videos
Properties of Organometallic Compounds
Diels–Alder Reaction: Characteristics of Dienophiles
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends on...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
Ziegler–Natta Chain-Growth Polymerization: Overview
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...

