New cleavage of the azirine ring by single electron transfer: The synthesis of 2H-imidazoles, pyridazines and pyrrolines

Authors
Auricchio, S Grassi, S Malpezzi, L Sartori, AS Truscello, AM
Citation
S. Auricchio et al., New cleavage of the azirine ring by single electron transfer: The synthesis of 2H-imidazoles, pyridazines and pyrrolines, EUR J ORG C, (6), 2001, pp. 1183-1187
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
6
Year of publication
2001
Pages
1183 - 1187
Database
ISI
SICI code
1434-193X(200103):6<1183:NCOTAR>2.0.ZU;2-0
Abstract
Here we report the first example of the dimerisation of azirines to 2H-imid azoles or 3,5-disubstituted pyridazines from a reaction promoted by FeCl2. An azirine complex with a radical structure is proposed as an intermediate. Cyclopropyl ke- tones and pyrrolines are isolated when the reaction is car ried out in the presence of styrenes.