Diaziridines are heterocyclic compound

Heterocyclic compound

A heterocyclic compound is a cyclic compound which has atoms of at least two different elements as members of its ring. The counterparts of heterocyclic compounds are homocyclic compounds, the rings of which are made of a single element....

s containing two nitrogen

Nitrogen

Nitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...

 atoms in a three-membered ring. They can be considered as strained hydrazine

Hydrazine

Hydrazine is an inorganic compound with the formula N2H4. It is a colourless flammable liquid with an ammonia-like odor. Hydrazine is highly toxic and dangerously unstable unless handled in solution. Approximately 260,000 tons are manufactured annually...

s. 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

Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups....

 compound is treated with ammonia

Ammonia

Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...

 or respectively a primary aliphatic amine

Amine

Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...

 and an aminating reagent like hydroxylamine-O-sulfonic acid (HOSA) under slightly basic conditions. The final step is based on the intramolecular cyclization of an aminal

Aminal

An aminal or aminoacetal is a functional group or type of chemical compound that has two amine groups attached to the same carbon atom: -C-. Again R can be hydrogen or an alkyl group....

.

Reactions

• Unsubstituted diaziridines are often directly oxidized (I₂/NEt₃) to the more stable diazirine
  Diazirine
  Diazirines are a class of organic molecules consisting of a carbon bound to two nitrogen atoms, which are double-bonded to each other, forming a cyclopropene-like ring...
  
  s.
• They can undergo ring expansion reaction with electrophilic reagents like ketene
  Ketene
  A ketene is an organic compound of the form R'RC=C=O. The term is also used specifically to mean ethenone, the simplest ketene, where R' and R are hydrogen atoms.Ketenes were first studied as a class by Hermann Staudinger.-Formation:...
  
  s or isocyanate
  Isocyanate
  Isocyanate is the functional group of elements –N=C=O , not to be confused with the cyanate functional group which is arranged as –O–C≡N or with isocyanide, R-N≡C. Any organic compound which contains an isocyanate group may also be referred to in brief as an isocyanate. An isocyanate may have more...
  
  s.
• Some derivatives are neurotropically active.