Azirine

Azirines are three-membered heterocyclic unsaturated (i.e. they contain a double bond) compounds containing a nitrogen atom and related to the saturated analogue aziridine.[1] They are highly reactive yet have been reported in a few natural products such as Dysidazirine. There are two isomers of azirine: 1H-azirine 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.[2] During this reaction, a nitrene is formed as an intermediate. Alternatively, they can be obtained by oxidation of the corresponding aziridine.

Reactions

Photolysis of azirines (under 300 nm) is a very efficient way to generate nitrile ylides. These nitrile ylides are dipolar compounds and can be trapped by a variety of dipolarophiles to yield heterocyclic compounds, e.g. pyrrolines.

The strained ring system also undergoes reactions that favor ring opening and can act as a nucleophile or an electrophile.

An azirine is an intermediate in the Neber rearrangement.

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gollark: It seems like *you're* interpreting things uncharitably at this point.
gollark: > the entire discussion broke out due to misunderstanding; and you claimed to purposefully understand me wrong: https://discord.com/channels/346530916832903169/348702212110680064/809474809301827595I do not think this is what they meant; presumably, they're more willing to charitably interpret things from people for whom that has been accurate in the past.
gollark: And you regularly insult Rust programmers similarly.
gollark: https://discord.com/channels/346530916832903169/348702212110680064/815547980886573076 isn't evidence, you just said "trolling".

References
  1. Teresa M. V. D. Pinho e Melo and Antonio M. d’A. Rocha Gonsalves (2004). "Exploiting 2-Halo-2H-Azirine Chemistry". Current Organic Synthesis. 1 (3): 275–292. doi:10.2174/1570179043366729. Archived from the original on 2006-09-28.
  2. Palacios F, Ochoa de Retana AM, Martinez de Marigorta E, de los Santos JM (2001). "2H-Azirines as synthetic tools in organic chemistry". Eur. J. Org. Chem. 2001 (13): 2401–2414. doi:10.1002/1099-0690(200107)2001:13<2401::AID-EJOC2401>3.0.CO;2-U.
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