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  • Title: Interactions of arenes and thioethers resulting in facilitated oxidation.
    Author: Chung WJ, Ammam M, Gruhn NE, Nichol GS, Singh WP, Wilson GS, Glass RS.
    Journal: Org Lett; 2009 Jan 15; 11(2):397-400. PubMed ID: 19102660.
    Abstract:
    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...pi interaction.
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