2012/03/22 by Eric A. Mercier, Chris Smith, Masood Parvez +1 · 1 citation
Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Chemical Synthesis and Reactions #Organoselenium and organotellurium chemistry #Sulfur-Based Synthesis Techniques
paper · doi:10.1021/jo300313v
openalex publication_date 2012/03/22 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/15
Cyclic seleninate esters serve as catalysts for the rapid oxidation of sulfides to sulfoxides, alkenes to epoxides, and enamines to α-hydroxyketones. Optimal conditions were found that minimize the overoxidation of the product sulfoxides to sulfones and the hydrolysis of epoxides to diols. In some examples such as styrene derivatives, oxidative cleavage was observed instead of epoxidation. The enamine oxidations proceed via the initial formation of dimeric 2,5-diamino-1,4-dioxane species, which were hydrolyzed in situ to the final products. The structure of one such dimer was confirmed by X-ray crystallography.