Related Experiment Video
Updated: Jun 10, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
A Lead(II) Substituted Triplet Carbene
Fabian Dankert1, Julian Messelberger1, Ugo Authesserre1
1Saarland University, Coordination Chemistry, Campus C4.1, D-66123 Saarbrücken, Germany.
Abstract:
Reaction of the pincer-type ligand L3 supported complex [L3PbBr][BArF24] (1) with Li[(C(═N2)TMS)] furnishes [L3Pb(C(═N2)TMS)][BArF24] (2). Diazo-compound 2 eliminates dinitrogen upon irradiation affording formal plumba-alkyne 3, which persists in cold fluoroarene solutions. Variable temperature UV/Vis and NMR spectroscopies in combination with quantum-chemical calculations identify 3 as a metal-substituted triplet carbene. In-crystallo irradiation of [L3Pb(C(═N2)TMS)(tol)][BArF24] (2·tol) provides a snapshot of intermolecular C-H bond insertion with toluene (4).
More Related Videos
09:45Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
Published on: March 20, 2017
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
Related Concept Videos
Carbocations
Nucleophilic Aromatic Substitution: Elimination–Addition
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Electrophilic Addition to Alkynes: Halogenation
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.