Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control
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- 作者：Takuhei Yamamoto ; Jixun Dai ; Neil E. Jacobsen ; Malika Ammam ; Gabriel B. Hall ; Olivier Mozziconacci ; Christian Schöneich ; George S. Wilson ; Richard S. Glass
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：August 5, 2016
- 年：2016
- 卷：18
- 期：15
- 页码：3522-3525
- 全文大小：290K
- 年卷期：0
- ISSN：1523-7052
文摘
The electrochemical oxidation of thioethers is shown to be facilitated by neighboring amide participation. 1H NMR spectroscopic analysis in acetonitrile solution of two conformationally constrained compounds with such facilitation shows that two-electron participation by the amide π2 orbital can occur to stabilize the developing sulfur radical cation.