Diaziridine

Diaziridines are heterocyclic compounds containing two nitrogen atoms in a three-membered ring.

Unlike most amine types of structures, the nitrogen atoms of diaziridines are configurationally stable because the ring strain prevents Walden inversion.

As a result, there can be various stereoisomeric 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.

[1] The final step is based on the intramolecular cyclization of an aminal.

Skeletal formula of diaziridine
Ball-and-stick model of the diaziridine molecule