Functionalized Diaziridines as Potential Electrophilic Aziridinating Agents

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Functionalized Diaziridines as Potential
Electrophilic Aziridinating Agents
Katherine L. Hervert, Department of Chemistry,
Ohio Wesleyan University

• The facile alkene oxidation to an epoxide is an
  excellent example of an extremely useful
  transformation that produces an intermediate that
  possesses unlimited synthetic utility.
• By modeling the dioxirane epoxidation reaction,
  we propose a simple, electrophilic aziridination
  methodology utilizing the diaziridine in lieu of
  the dioxirane.

The reaction of trans-stillbene with
electrophilic diaziridine 1 was investigated
using several Cu(I) catalysts and salen
complexes. IIt was found that the aziridine 3
was not yet formed under the examined reaction
conditions.