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

doi:10.1021/ol802683s

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

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

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 language	English (US)
Pages (from-to)	397-400
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	2
DOIs	https://doi.org/10.1021/ol802683s
State	Published - Jan 15 2009

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol802683s

Cite this

@article{c3dcd578ec754a83870dcd02aa9fd34b,

title = "Interactions of arenes and thioethers resulting in facilitated oxidation",

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.",

author = "Chung, {Woo Jin} and Malika Ammam and Gruhn, {Nadine E.} and Nichol, {Gary S.} and Singh, {Waheguru P.} and Wilson, {George S.} and Glass, {Richard S.}",

year = "2009",

month = jan,

day = "15",

doi = "10.1021/ol802683s",

language = "English (US)",

volume = "11",

pages = "397--400",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "2",

}

TY - JOUR

T1 - Interactions of arenes and thioethers resulting in facilitated oxidation

AU - Chung, Woo Jin

AU - Ammam, Malika

AU - Gruhn, Nadine E.

AU - Nichol, Gary S.

AU - Singh, Waheguru P.

AU - Wilson, George S.

AU - Glass, Richard S.

PY - 2009/1/15

Y1 - 2009/1/15

N2 - (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.

AB - (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.

UR - http://www.scopus.com/inward/record.url?scp=61449211129&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=61449211129&partnerID=8YFLogxK

U2 - 10.1021/ol802683s

DO - 10.1021/ol802683s

M3 - Article

C2 - 19102660

AN - SCOPUS:61449211129

SN - 1523-7060

VL - 11

SP - 397

EP - 400

JO - Organic Letters

JF - Organic Letters

IS - 2

ER -

Interactions of arenes and thioethers resulting in facilitated oxidation

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 725652: Experimental Crystal Structure Determination

Cite this

Interactions of arenes and thioethers resulting in facilitated oxidation

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 725652: Experimental Crystal Structure Determination

Cite this