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

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

(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 (US)
Pages (from-to)397-400
Number of pages4
JournalOrganic Letters
Volume11
Issue number2
DOIs
StatePublished - Jan 15 2009

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Heptanes
Photoelectron Spectroscopy
electrochemical oxidation
Ionization potential
Electrochemical oxidation
Sulfides
Photoelectron spectroscopy
heptanes
Cyclic voltammetry
electron transfer
photoelectron spectroscopy
Electrons
analogs
ionization
Oxidation
oxidation
synthesis
interactions
energy

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Chung, W. J., Ammam, M., Gruhn, N. E., Nichol, G. S., Singh, W. P., Wilson, G. S., & Glass, R. S. (2009). Interactions of arenes and thioethers resulting in facilitated oxidation. Organic Letters, 11(2), 397-400. https://doi.org/10.1021/ol802683s

Interactions of arenes and thioethers resulting in facilitated oxidation. / Chung, Woo Jin; Ammam, Malika; Gruhn, Nadine E.; Nichol, Gary S.; Singh, Waheguru P.; Wilson, George S.; Glass, Richard S.

In: Organic Letters, Vol. 11, No. 2, 15.01.2009, p. 397-400.

Research output: Contribution to journalArticle

Chung, WJ, Ammam, M, Gruhn, NE, Nichol, GS, Singh, WP, Wilson, GS & Glass, RS 2009, 'Interactions of arenes and thioethers resulting in facilitated oxidation', Organic Letters, vol. 11, no. 2, pp. 397-400. https://doi.org/10.1021/ol802683s
Chung WJ, Ammam M, Gruhn NE, Nichol GS, Singh WP, Wilson GS et al. Interactions of arenes and thioethers resulting in facilitated oxidation. Organic Letters. 2009 Jan 15;11(2):397-400. https://doi.org/10.1021/ol802683s
Chung, Woo Jin ; Ammam, Malika ; Gruhn, Nadine E. ; Nichol, Gary S. ; Singh, Waheguru P. ; Wilson, George S. ; Glass, Richard S. / Interactions of arenes and thioethers resulting in facilitated oxidation. In: Organic Letters. 2009 ; Vol. 11, No. 2. pp. 397-400.
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