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. <sup>1sup>H NMR spectroscopic analysis in acetonitrile solution of two conformationally constrained compounds with such facilitation shows that two-electron participation by the amide π<sub>2sub> orbital can occur to stabilize the developing sulfur radical cation.