Diaziridine

Names

IUPAC name

Diaziridine

Identifiers

3D model (Jmol)

4236879^N

InChI=1S/CH4N2/c1-2-3-1/h2-3H,1H2^N
Key: DIXBSCZRIZDQGC-UHFFFAOYSA-N^N
InChI=1/CH4N2/c1-2-3-1/h2-3H,1H2
Key: DIXBSCZRIZDQGC-UHFFFAOYAM

SMILES

N1NC1

Properties

Chemical formula

CH₄N₂

Molar mass

44.06 g·mol⁻¹

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

Diaziridines are heterocyclic compounds containing two nitrogen atoms in a three-membered ring. They can be considered as strained hydrazines. Due to the ring strain, the nitrogen atoms are configuration stable leading to cis-trans isomers. They are usually synthesized by a method developed by E. Schmitz: A carbonyl compound is treated with ammonia or respectively a primary aliphatic amine and an aminating reagent like hydroxylamine-O-sulfonic acid (HOSA) 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 are neurotropically active.

References

↑ 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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