Azirine

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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.

[edit] References

  1. ^ Teresa M. V. D. Pinho e Melo and Antonio M. d’A. Rocha Gonsalves. Current Organic Synthesis, Volume 1, No. 3, 2004 Pp.275-292 "Exploiting 2-Halo-2H-Azirine Chemistry" See abstract: [1]