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Updated: Nov 27, 2025

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles
Lars E Sattler1, Gerhard Hilt1
1Institut für Chemie, Oldenburg University, Carl-von-Ossietzky-Strasse 9-11, 26111, Oldenburg, Germany.
Abstract:
The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.
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