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.

Multimodal Reactivity of N-H Bonds in Triazanes and Isolation of a Triazinyl Radical.

The employment of nitrogen Lewis acids based on nitrenium cations has been increasingly featured in the fields of main group chemistry and catalysis. A formally reduced form of nitrenium ─cyclic triazanes ─are intriguing chemical compounds, the chemistry of which is completely unexplored. In this work, we reveal that N-H-triazanes exhibit unusual N-H bond properties; namely, they can serve as protons, hydrides, or hydrogen atom donors.

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.