Azirine

Azirine
Names
	IUPAC name 1H-Azirine
Identifiers
CAS Number	157-17-5;
3D model (JSmol)	Interactive image;
PubChem CID	5461042;
	SMILES C1=CN1;
Properties
Chemical formula	C2H3N
Molar mass	41.05 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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 are found in a number of natural products such as the antibiotic azirinomycin, isolated from Streptomyces auras.

The strained ring system undergoes reactions that favor ring opening and can act as a nucleophile or an electrophile. An azirine is an intermediate in the Neber rearrangement.

References

^ 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.

[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.

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