Related Experiment Video
Updated: Jun 27, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
2:1 Adducts Arising from Reactions between Benzynes and 1,3,4-Oxadiazoles
Alexander L Guzman1, Paul V Kevorkian1, Thomas R Hoye1
1Department of Chemistry, University of Minnesota, 207 Pleasant Street Southeast, Minneapolis, Minnesota 55455, United States.
Abstract:
2:1 adducts arise from the reaction of 2,5-diaryl-1,3,4-oxadiazoles and benzynes generated from the hexadehydro-Diels-Alder (HDDA) reaction. Density functional theory computations support a mechanistic manifold that includes a concerted SNAr process. Additionally, the benzyne trapping reaction of 2,5-dimethyl-1,3,4-oxadiazole affords an unusual acylimine-containing 2:1 adduct, which is the first case in which a dearomatized product has arisen from a HDDA reaction.
More Related Videos
05:34Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
Related Concept Videos
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene
Reactions at the Benzylic Position: Oxidation and Reduction
Structure of Benzene: Kekulé Model
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
Nucleophilic Aromatic Substitution: Elimination–Addition
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds