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

Research output: Contribution to journalArticle

2 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)3522-3525
Number of pages4
JournalOrganic Letters
Volume18
Issue number15
DOIs
StatePublished - Aug 5 2016

Fingerprint

Sulfides
Amides
amides
Oxidation
oxidation
Spectroscopic analysis
electrochemical oxidation
Electrochemical oxidation
spectroscopic analysis
Sulfur
acetonitrile
Cations
sulfur
Nuclear magnetic resonance
Electrons
cations
orbitals
nuclear magnetic resonance
electrons
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Yamamoto, T., Dai, J., Jacobsen, N. E., Ammam, M., Hall, G. B., Mozziconacci, O., ... Glass, R. S. (2016). Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control. Organic Letters, 18(15), 3522-3525. https://doi.org/10.1021/acs.orglett.6b01309

Neighboring π-Amide Participation in Thioether Oxidation : Conformational Control. / Yamamoto, Takuhei; Dai, Jixun; Jacobsen, Neil E.; Ammam, Malika; Hall, Gabriel B.; Mozziconacci, Olivier; Schöneich, Christian; Wilson, George S.; Glass, Richard S.

In: Organic Letters, Vol. 18, No. 15, 05.08.2016, p. 3522-3525.

Research output: Contribution to journalArticle

Yamamoto, T, Dai, J, Jacobsen, NE, Ammam, M, Hall, GB, Mozziconacci, O, Schöneich, C, Wilson, GS & Glass, RS 2016, 'Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control', Organic Letters, vol. 18, no. 15, pp. 3522-3525. https://doi.org/10.1021/acs.orglett.6b01309
Yamamoto T, Dai J, Jacobsen NE, Ammam M, Hall GB, Mozziconacci O et al. Neighboring π-Amide Participation in Thioether Oxidation: Conformational Control. Organic Letters. 2016 Aug 5;18(15):3522-3525. https://doi.org/10.1021/acs.orglett.6b01309
Yamamoto, Takuhei ; Dai, Jixun ; Jacobsen, Neil E. ; Ammam, Malika ; Hall, Gabriel B. ; Mozziconacci, Olivier ; Schöneich, Christian ; Wilson, George S. ; Glass, Richard S. / Neighboring π-Amide Participation in Thioether Oxidation : Conformational Control. In: Organic Letters. 2016 ; Vol. 18, No. 15. pp. 3522-3525.
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