1.
J Org Chem
; 83(19): 12000-12006, 2018 Oct 05.
Artigo
em Inglês
| MEDLINE
| ID: mdl-30160966
RESUMO
The discovery that the Newman-Kwart rearrangement can be performed at room temperature by action of a simple and readily available oxidant, cerium ammonium nitrate, is described. The conditions give clean conversion when using electron-rich aromatic substrates, and the reactions are often quantitative. Computational studies support a reaction mechanism where the O-thiocarbamate is first oxidized to the radical cation, followed by nucleophilic attack by the ipso carbon of the aromatic system.