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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

(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
Pages (from-to)397-400
Number of pages4
JournalOrganic letters
Volume11
Issue number2
DOIs
Publication statusPublished - 15 Jan 2009

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