Diaziridine

 ( Nitrogen Heterocycles ) 

A diaziridine is a heterocyclic compound containing two nitrogen atoms in a three-membered ring. Diaziridines can be considered as strained . Unlike most amine types of structures, the nitrogen atoms of diaziridines are stereocenter stable because the ring strain prevents Walden inversion. As a result, there can be various forms of this structure.

They are usually synthesized by treating a carbonyl compound with an aminating reagent like hydroxylamine- O-sulfonic acid and either ammonia or a primary aliphatic amine under slightly basic conditions.Synthesis of monocyclic diaziridines and their fused derivatives; N. N. Makhova, V. Y. Petukhova, V. V. Kuznetsov, Arkivoc, 2008(i), 128-152.[1] The final step is based on the intramolecular cyclization of an aminal.

• Unsubstituted diaziridines are often directly oxidized (I₂/NEt₃) to the more stable .
• They can undergo ring expansion reaction with electrophilic reagents like or .
• Some derivatives have neurologic activity.