Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control

• DOI: 10.1021/acs.orglett.6b01309
• Publication Date: 2016-07-12T10:37:04Z
• Authors: Takuhei Yamamoto; Jixun Dai; Neil E. Jacobsen; Malika Ammam; Gabriel B. Hall; Olivier Mozziconacci; Christian Schöneich; George S. Wilson; Richard S. Glass
• Keywords: Thioether; Amide

The electrochemical oxidation of thioethers is shown to be facilitated by neighboring amide participation. 1H NMR spectroscopic analysis in acetonitrile solution two conformationally constrained compounds with such facilitation shows that two-electron participation the π2 orbital can occur stabilize developing sulfur radical cation.