Diaziridine

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.

Not to be confused with Diazirine.
Diaziridine
Skeletal formula of diaziridine
Ball-and-stick model of the diaziridine molecule
Names
Preferred IUPAC name
Diaziridine
Systematic IUPAC name
Diazacyclopropane
Other names
Diazirane
1,2-Diazacyclopropane
Identifiers
3D model (JSmol)
ChemSpider
Properties
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).
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Infobox references

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.[2]

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