Azirine

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Structural formula
Structural formula of azirine
General
Surname Azirine
other names

2 H azirine

Molecular formula C 2 H 3 N
External identifiers / databases
CAS number
  • 157-16-4 (2 H -azirine)
  • 157-17-5 (1 H -azirine)
PubChem 135972
ChemSpider 119750
Wikidata Q424273
properties
Molar mass 41.05 g mol −1
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

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

Manufacturing

The preparation of 2 H -azirine can be obtained from vinyl azide at reduced pressure and elevated temperature. Acetonitrile and ketenimine are formed as by-products .

Synthesis of azirine

properties

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

The azirine cation is the smallest heterocyclic aromatic compound.

Mesomeric stabilization of the azirinium cation

Reactions

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

Azirine derivatives arise as intermediates in the Neber rearrangement .

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ a b J.-C. Guillemin, J.-M. Denis, M.-C. Lasne, J.-L. Ripoll in: Tetrahedron 1988, 44 (14), 4447-4456. doi : 10.1016 / S0040-4020 (01) 86146-9