Triazenolysis of alkenes as an aza version of ozonolysis.

Alkenes are broadly used in synthetic applications, thanks to their abundance and versatility. Ozonolysis is one of the most canonical transformations that converts alkenes into molecules bearing carbon-oxygen motifs via C=C bond cleavage. Despite its extensive use in both industrial and laboratory settings, the aza version-cleavage of alkenes to form carbon-nitrogen bonds-remains elusive.

Triazolium Salts as Lewis Acid Catalysts.

We describe a new type of nitrenium-based Lewis acids: tetraaryl-1,2,3-triazolium salts. These were fully characterized by NMR and X-ray crystallography. The Gutmann-Beckett acidity numbers were determined to be up to 35.