| 词条 | Azirine |
| 释义 |
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 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. Preparation2H-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. {{clear|left}} ReactionsPhotolysis 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. References1. ^{{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|deadurl=yes|archiveurl=https://web.archive.org/web/20060928104209/http://bentham.org/cos/contabs/cos1-3.htm|archivedate=2006-09-28 |df=}} 2. ^{{cite journal|title=2H-Azirines as synthetic tools in organic chemistry|vauthors=Palacios F, Ochoa de Retana AM, Martinez de Marigorta E, de los Santos JM|journal=Eur. J. Org. Chem.|year=2001|pages=2401–2414|doi=10.1002/1099-0690(200107)2001:13<2401::AID-EJOC2401>3.0.CO;2-U|volume=2001|issue=13}} 3 : Nitrogen heterocycles|Imines|Three-membered rings |
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