Diaziridine

Diaziridine
Names
	Preferred IUPAC name Diaziridine
	Systematic IUPAC name Diazacyclopropane
	Other names Diazirane; 1,2-Diazacyclopropane
Identifiers
CAS Number	463-64-9 ;
3D model (JSmol)	Interactive image ;
ChemSpider	4236879 ;
PubChem CID	5059686 ;
CompTox Dashboard (EPA)	DTXSID701029321 ;
	InChI InChI=1S/CH4N2/c1-2-3-1/h2-3H,1H2 Key: DIXBSCZRIZDQGC-UHFFFAOYSA-N ; InChI=1/CH4N2/c1-2-3-1/h2-3H,1H2 Key: DIXBSCZRIZDQGC-UHFFFAOYAM;
	SMILES N1NC1;
Properties
Chemical formula	CH4N2
Molar mass	44.057 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Last updated May 06, 2025

A diaziridine is a heterocyclic compound containing two nitrogen atoms in a three-membered ring. Diaziridines can be considered as strained hydrazines. 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.

Reactions

Unsubstituted diaziridines are often directly oxidized (I₂/NEt₃) to the more stable diazirines.
They can undergo ring expansion reaction with electrophilic reagents like ketenes or isocyanates.
Some derivatives have neurologic activity.^[1]

References

1 2 Synthesis of monocyclic diaziridines and their fused derivatives; N. N. Makhova, V. Y. Petukhova, V. V. Kuznetsov, Arkivoc, 2008(i), 128-152.

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[Makhova2008-1] 1 2 Synthesis of monocyclic diaziridines and their fused derivatives; N. N. Makhova, V. Y. Petukhova, V. V. Kuznetsov, Arkivoc, 2008(i), 128-152.

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