Organic letters

An unusual radical smiles rearrangement

E Bacqué, M El Qacemi, SZ Zard

Index: Bacque, Eric; El Qacemi, Myriem; Zard, Samir Z. Organic Letters, 2005 , vol. 7, # 17 p. 3817 - 3820

Full Text: HTML

Citation Number: 47

Abstract

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 ...