Neighboring the effect in the oxidation of α-Stannyl phenyl vinyl sulfides

Richard S Glass, Qin Guo, Yunqi Liu

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

α-Stannyl vinyl sulfides were generally prepared by hydrostannylation of thioacetylenes catalyzed by Pd(PPh3)4. The regio- and stereochemistry of the products was determined unequivocally in three cases by X-ray crystallographic structure studies and in the others by 1H NMR spectroscopic analysis. The irreversible oxidation potentials of these compounds were determined in acetonitrile and dichloromethane by cyclic voltammetry. The oxidation potentials provide evidence for significant interaction between the C-Sn σ band and sulfur 3p lone pair orbital in cases with appropriate geometry.

Original languageEnglish (US)
Pages (from-to)12273-12286
Number of pages14
JournalTetrahedron
Volume53
Issue number36
DOIs
StatePublished - Sep 8 1997

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Methylene Chloride
Sulfides
Sulfur
X-Rays
Oxidation
Stereochemistry
Spectroscopic analysis
Cyclic voltammetry
Nuclear magnetic resonance
X rays
Geometry
acetonitrile
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Neighboring the effect in the oxidation of α-Stannyl phenyl vinyl sulfides. / Glass, Richard S; Guo, Qin; Liu, Yunqi.

In: Tetrahedron, Vol. 53, No. 36, 08.09.1997, p. 12273-12286.

Research output: Contribution to journalArticle

Glass, Richard S ; Guo, Qin ; Liu, Yunqi. / Neighboring the effect in the oxidation of α-Stannyl phenyl vinyl sulfides. In: Tetrahedron. 1997 ; Vol. 53, No. 36. pp. 12273-12286.
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