Interactions of Arenes and Thioethers Resulting in Facilitated Oxidation
By Chung, Woo Jin; Ammam, Malika; Gruhn, Nadine E.; Nichol, Gary S.; Singh, Waheguru P.; Wilson, George S. & Glass, Richard S.
Published in Organic Letters
NULL
2009
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···π interaction.
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