Azirine

Azirine

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ImageFile=Azarines.svg
ImageSize=100px
IUPACName=1"H"-Azirine
OtherNames=
Section1=Chembox Identifiers
CASNo=157-17-5
PubChem=5461042
SMILES=C1=CN1
Section2=Chembox Properties
Formula=C2H3N
MolarMass=41.05 g/mol
Appearance=
Density=
MeltingPt=
BoilingPt=
Solubility=
Section3=Chembox Hazards
MainHazards=
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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. [cite journal | author = Teresa M. V. D. Pinho e Melo and Antonio M. d’A. Rocha Gonsalves | journal = Current Organic Synthesis | volume =1 | issue = 3 | year = 2004 | pages = 275–292 | title = Exploiting 2-Halo-2H-Azirine Chemistry | url = http://www.bentham.org/cos/contabs/cos1-3.htm#5 | doi = 10.2174/1570179043366729] 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


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