An Unusual Radical Smiles Rearrangement

Autor: Bacque, E., Qacemi, M. El, Zard, S. Z.
Zdroj: Organic Letters; August 2005, Vol. 7 Issue: 17 p3817-3820, 4p
Abstrakt: Radicals derived from N-(α-xanthyl)acetanilides or N-(α-xanthyl)acetylaminopyridines possessing a substituent next to the nitrogen undergo a hitherto undocumented Smiles rearrangement proceeding through a four-membered ring. It was also found that under certain conditions the amidyl radical produced by cleavage of the four-membered ring intermediate can undergo fragmentation to give an isocyanate. Such fragmentations are unprecedented at temperatures corresponding to refluxing benzene or chlorobenzene.
Databáze: Supplemental Index