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 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.
Chung
Woo Jin
WJ
Department of Chemistry, The University of Arizona, Tucson, Arizona 85721, USA.
Ammam
Malika
M
Gruhn
Nadine E
NE
Nichol
Gary S
GS
Singh
Waheguru P
WP
Wilson
George S
GS
Glass
Richard S
RS
D004563:Electrochemistry; D047028:Macrocyclic Compounds / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013440:Sulfides / Q000737:chemistry*
D047028:Macrocyclic Compounds; D013440:Sulfides