The reaction of phenyl azide with olefins

5-Azido-4-dimethylamino-1-methyl-1,2,4-triazolium Hexafluoridophosphate and Derivatives

“…The well-known versatility of azide chemistry [22] motivated us to attempt exemplary reactions of 1. Thus, dipolar cycloaddition of azides with alkenes is known to produce 1,2,3-triazolines or aziridines [23]. In our hands, strained bicycloheptene (norbornene) [24,25] reacted with azidotriazolium salt 1 to give the tricyclic aziridine 2 in acceptable yield.…”

Polyaddition of Azide‐Containing Norbornene‐Based Monomer through Strain‐Promoted 1,3‐Dipolar Cycloaddition Reaction

“…As a unique feature, triazoline can eliminate N 2 when exposed to light, heat, or catalyzed by acid, cobalt, or ruthenium . The decomposition of triazoline to afford aziridine, imine, and amine has been briefly reviewed and also observed by Hobbs et al in their experiments .…”

“…The reaction was first reported by Wolff in 1912 where phenyl azide and aniline were used to make triazoline, and it is generally believed to be concerted . But, triazoline is not stable and subjected to decomposition at intermediate temperatures to eliminate N 2 molecule . For example, Garcia‐Garibay and co‐workers applied photo‐ and thermal‐induced denitrogenation on the solid state of crystalline triazoline, the quantitative formation of aziridines could lead to reconstructive phase transition as an interesting example of solid‐to‐solid transformation .…”

Co(porphyrin)-catalysed amination of 1,2-dihydronaphthalene derivatives by aryl azides

“…Compound 1 was not detected. It is well known that the non-catalysed reaction between olefins and organic azides [19,34,35] affords imines by thermal decomposition of 1,2,3-triazolines, therefore we proposed a blank reaction mechanism illustrated in Scheme 4.…”

“…The lack of formation of 2,3-dihydro-N-(4-nitrophenyl)-1H-inden-1-amine (18) confirmed that cobalt porphyrins are not competent catalysts for the direct CeH amination of a-substituted cyclic styrenes. Thus, when a hydrogen atom abstraction is impossible the uncatalysed reaction is the only achievable process [34]. It should be noted that the ruthenium porphyrin mediated CeH amination of indene yielded 18 in moderate yields [12].…”