Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control

Takuhei Yamamoto; Jixun Dai; Neil E. Jacobsen; Malika Ammam; Gabriel B. Hall; Olivier Mozziconacci; Christian Schöneich; George S. Wilson; Richard S. Glass

doi:10.1021/acs.orglett.6b01309

Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control

Takuhei Yamamoto, Jixun Dai, Neil E. Jacobsen, Malika Ammam, Gabriel B. Hall, Olivier Mozziconacci, Christian Schöneich, George S. Wilson, Richard S. Glass

Chemistry and Biochemistry

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

4 Scopus citations

Abstract

The electrochemical oxidation of thioethers is shown to be facilitated by neighboring amide participation. ¹H NMR spectroscopic analysis in acetonitrile solution of two conformationally constrained compounds with such facilitation shows that two-electron participation by the amide π₂ orbital can occur to stabilize the developing sulfur radical cation.

Original language	English (US)
Pages (from-to)	3522-3525
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.6b01309
State	Published - Aug 5 2016

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.6b01309

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title = "Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control",

abstract = "The electrochemical oxidation of thioethers is shown to be facilitated by neighboring amide participation. 1H NMR spectroscopic analysis in acetonitrile solution of two conformationally constrained compounds with such facilitation shows that two-electron participation by the amide π2 orbital can occur to stabilize the developing sulfur radical cation.",

author = "Takuhei Yamamoto and Jixun Dai and Jacobsen, {Neil E.} and Malika Ammam and Hall, {Gabriel B.} and Olivier Mozziconacci and Christian Sch{\"o}neich and Wilson, {George S.} and Glass, {Richard S.}",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = aug,

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doi = "10.1021/acs.orglett.6b01309",

language = "English (US)",

volume = "18",

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TY - JOUR

T1 - Neighboring π-Amide Participation in Thioether Oxidation

T2 - Conformational Control

AU - Yamamoto, Takuhei

AU - Dai, Jixun

AU - Jacobsen, Neil E.

AU - Ammam, Malika

AU - Hall, Gabriel B.

AU - Mozziconacci, Olivier

AU - Schöneich, Christian

AU - Wilson, George S.

AU - Glass, Richard S.

PY - 2016/8/5

Y1 - 2016/8/5

N2 - The electrochemical oxidation of thioethers is shown to be facilitated by neighboring amide participation. 1H NMR spectroscopic analysis in acetonitrile solution of two conformationally constrained compounds with such facilitation shows that two-electron participation by the amide π2 orbital can occur to stabilize the developing sulfur radical cation.

AB - The electrochemical oxidation of thioethers is shown to be facilitated by neighboring amide participation. 1H NMR spectroscopic analysis in acetonitrile solution of two conformationally constrained compounds with such facilitation shows that two-electron participation by the amide π2 orbital can occur to stabilize the developing sulfur radical cation.

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U2 - 10.1021/acs.orglett.6b01309

DO - 10.1021/acs.orglett.6b01309

M3 - Article

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VL - 18

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EP - 3525

JO - Organic Letters

JF - Organic Letters

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ER -

Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control

Abstract

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CCDC 1500899: Experimental Crystal Structure Determination

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Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control

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CCDC 1500899: Experimental Crystal Structure Determination

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