Related Experiment Video
Updated: Dec 23, 2025

Merging Ion Concentration Polarization between Juxtaposed Ion Exchange Membranes to Block the Propagation of the Polarization Zone
Published on: February 23, 2017
Reagent Control Enables Selective and Regiodivergent Opening of Unsymmetrical Phenonium Ions
Shiyan Xu1, Hannah M Holst1, Shelby B McGuire1
1Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
Abstract:
We report the first examples of selective and regiodivergent opening of unsymmetrical phenonium ions with chloride ions. These reactions are enabled by the dual role of SnCl4 and TiCl4 as Lewis acids and chloride nucleophiles. Reagent control dictates addition of chloride at either the substituted internal position (SnCl4) or unsubstituted terminal position (TiCl4) of the phenonium ion. These reactions are highly selective, stereospecific, operationally simple, and proceed in good to excellent yields. Diverse product utility is demonstrated.
More Related Videos
07:50Plasmid-derived DNA Strand Displacement Gates for Implementing Chemical Reaction Networks
Published on: November 25, 2015
10:52Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
Published on: July 27, 2022
Related Concept Videos
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Regioselectivity of Electrophilic Additions-Peroxide Effect
ortho–para-Directing Deactivators: Halogens
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Ion Exchange