Related Experiment Video
Updated: Feb 5, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Pummerer Cyclization Revisited: Unraveling of Acyl Oxonium Ion and Vinyl Sulfide Pathways
1Department of Chemistry , Oregon State University , Corvallis , Oregon 97331 , United States.
Abstract:
Two viable pathways (vinyl sulfide and acyl oxonium ion) for the Pummerer cyclization have been unraveled that expand the reaction scope and capabilities. Use of Brønsted- enhanced Lewis acidity was key to realization of the vinyl sulfide pathway, whereas selective complexation of the sulfur lone pair facilitated the unprecedented acyl oxonium ion pathway. Preliminary mechanistic investigations support these hypotheses. A range of substrates have been explored to understand the reaction parameters.
Related Concept Videos
Formation of Complex Ions
Preparation and Reactions of Sulfides
Structure and Nomenclature of Thiols and Sulfides
Common Ion Effect
Precipitation of Ions
The equation that describes the equilibrium between solid calcium carbonate and its solvated ions is:
Ion Channels
Ion channels are specialized integral membrane proteins on the plasma membrane that allow...

