Diaziridine

Diaziridine
IUPAC name Diaziridine
Identifiers
PubChem	5059686
Jmol-3D images	Image 1
SMILES C1NN1
Properties
Molecular formula	CH4N2
Molar mass	44.06 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

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