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Nitrene insertion reactions are arguably the most atom-economical method for the creation of carbon-nitrogen bonds. Despite challenges associated with control and selectivity in nitrene chemistry, progress within this research area remains robust. Our work explores the in situ oxidation methods for nitrene formation from carbamate starting materials, followed by a study in the selectivity of alkene aziridination. Transition metal catalysts, especially dirhodium complexes, have been reported for their catalytic activity in these reactions. Dirhodium complexes are well suited for activation and functionalization of nitrenes due to the adequate stabilization they provide to the rhodium-nitrene species. Our research utilizes phenyl and benzyl carbamates as starting compounds for an optimized intramolecular N-insertion onto a substituted, electron-rich alkene. Preliminary results show that substitution of the alkene and choice of a hypervalent iodine oxidant, with or without a dirhodium catalyst, are important in the spectroscopic observation and subsequent isolation of aziridine products. Substrate design, reaction optimization, mechanistic insights, and the scope and limitations of our methodology are discussed.
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Lasky, Matthew Richard, "A Study of C-N Bond Formation: Intramolecular Aziridination of Alkenes via Carbamate-Derived Nitrene Intermediates" (2018). Senior Projects Spring 2018. 46.
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