Interactions of arenes and thioethers resulting in facilitated oxidation

Woo Jin Chung, Malika Ammam, Nadine E. Gruhn, Gary S. Nichol, Waheguru P. Singh, George S. Wilson, Richard S. Glass

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

(Figure Presented) Synthesis of 6-endo and 6-exomethylthio-2- endoarylbicyclo[2.2.1]heptanes was accomplished stereoselectively. The ionization energies, determined by photoelectron spectroscopy, and electrochemical oxidation potentials, determined by cyclic voltammetry, were lower for the 6-endomethylthio compounds than for their 6-exomethylthio analogues. Calculations supported the notion that facilitation of electron transfer in the 6-endomethylthio compounds results from through-space S⋯π interaction.

Original languageEnglish (US)
Pages (from-to)397-400
Number of pages4
JournalOrganic Letters
Volume11
Issue number2
DOIs
StatePublished - Jan 15 2009

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Chung, W. J., Ammam, M., Gruhn, N. E., Nichol, G. S., Singh, W. P., Wilson, G. S., & Glass, R. S. (2009). Interactions of arenes and thioethers resulting in facilitated oxidation. Organic Letters, 11(2), 397-400. https://doi.org/10.1021/ol802683s