Related Experiment Video
Updated: Sep 28, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis of N-tosylaziridines from substituted alkenes via zirconooxaziridine catalysis
Ali A Pinarci1, Noah Daniecki1, Tyler M TenHoeve1
1Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, NJ, USA. moura-letts@rowan.edu.
Abstract:
Herein we report the zirconooxaziridine promoted aziridination of alkenes using chloramine T as the quantitative source of N. The reaction works with high yields, diastereoselectivities and stereospecificity for a wide variety of substituted alkenes. A potential mechanism involving the formation of a zirconooxaziridine complex as the active catalyst has been proposed and initial mechanistic data would indicate that a highly associative mechanism is the predominant pathway for this transformation.
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

