Azirine

2H- azirine

Template: Infobox chemical / molecular formula search available

Azirine, more specifically 2H- azirine, the simplest unsaturated nitrogen-containing three-membered heterocycle. It belongs to the tribe heterocyclic systems and the class of cyclic imines. The saturated analogue is aziridine, the carbocyclic analogue is cyclopropene. The isomeric 1H- azirine which carries the proton on the nitrogen atom is not stable, and is isomerized to the 2H- azirine.

Production

The preparation of 2H- azirine can be obtained at a reduced pressure and increased temperature from vinyl azide. Byproducts of acetonitrile and ketenimine.

Properties

The absorption maximum is in pentane in the ultraviolet region at a wavelength of λ = 229 nm

The cation of the azirine is the smallest heterocyclic aromatic compound.

Reactions

Azirine is due to its high ring strain very reactive. It reacts with electrophiles and nucleophiles with ring opening.

Derivatives of azirine arise as intermediates of Neber rearrangement.