Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control

Takuhei Yamamoto, Jixun Dai, Neil E. Jacobsen, Malika Ammam, Gabriel B. Hall, Olivier Mozziconacci, Christian Schöneich, George S. Wilson, Richard S. Glass

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)3522-3525
Number of pages4
JournalOrganic Letters
Volume18
Issue number15
DOIs
StatePublished - Aug 5 2016

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Yamamoto, T., Dai, J., Jacobsen, N. E., Ammam, M., Hall, G. B., Mozziconacci, O., Schöneich, C., Wilson, G. S., & Glass, R. S. (2016). Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control. Organic Letters, 18(15), 3522-3525. https://doi.org/10.1021/acs.orglett.6b01309