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New Cleavage of the Azirine Ring by Single Electron Transfer: The Synthesis of 2 H ‐Imidazoles, Pyridazines and Pyrrolines
Author(s) -
Auricchio Sergio,
Grassi Simona,
Malpezzi Luciana,
Sarzi Sartori Attilio,
Truscello Ada M.
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200103)2001:6<1183::aid-ejoc1183>3.0.co;2-g
Subject(s) - azirine , chemistry , cleavage (geology) , ring (chemistry) , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering
Here we report the first example of the dimerisation of azirines to 2 H ‐imidazoles or 3,5‐disubstituted pyridazines from a reaction promoted by FeCl 2 . An azirine complex with a radical structure is proposed as an intermediate. Cyclopropyl ketones and pyrrolines are isolated when the reaction is carried out in the presence of styrenes.