2H-azirine
Sign in to saveAzirine is three-membered heterocyclic unsaturated (i.e. it contain a double bond) compound containing a nitrogen atom and related to the saturated analogue aziridine. Azirines are highly reactive yet have been reported in a few natural products such as Dysidazirine. There are two isomers of azirine: 1H-Azirines with a carbon-carbon double bond are not stable and rearrange to the tautomeric 2H-azirine, a compound with a carbon-nitrogen double bond. 2H-Azirines can be considered strained imines and are isolable.
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4 sectionsContents
- Preparation
- Reactions
- See also
- References
Azirine is three-membered heterocyclic unsaturated (i.e. it contain a double bond) compound containing a nitrogen atom and related to the saturated analogue aziridine. Azirines are highly reactive yet have been reported in a few natural products such as Dysidazirine. There are two isomers of azirine: 1H-Azirines with a carbon-carbon double bond are not stable and rearrange to the tautomeric 2H-azirine, a compound with a carbon-nitrogen double bond. 2H-Azirines can be considered strained imines and are isolable.
== Preparation== 2H-Azirine is most often obtained by the thermolysis of vinyl azides. During this reaction, a nitrene is formed as an intermediate. Alternatively, they can be obtained by oxidation of the corresponding aziridine. Azirine can be generated during photolysis of isoxazole. Due to the weak N-O bond, the isoxazole ring tends to collapse under UV irradiation, rearranging to azirine. 350px|Azirine synthesis