Interactions of Arenes and Thioethers Resulting in Facilitated Oxidation

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 th...

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Bibliographic Details
Published in:Organic letters 2009-01, Vol.11 (2), p.397-400
Main Authors: Chung, Woo Jin, Ammam, Malika, Gruhn, Nadine E, Nichol, Gary S, Singh, Waheguru P, Wilson, George S, Glass, Richard S
Format: Article
Language:English
Subjects:
Electrochemistry
Macrocyclic Compounds - chemistry
Models, Molecular
Molecular Conformation
Oxidation-Reduction
Sulfides - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol802683s