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

Richard S. Glass; Qin Guo; Yunqi Liu

doi:10.1016/S0040-4020(97)00559-0

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

Richard S. Glass, Qin Guo, Yunqi Liu

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

19 Scopus citations

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 language	English (US)
Pages (from-to)	12273-12286
Number of pages	14
Journal	Tetrahedron
Volume	53
Issue number	36
DOIs	https://doi.org/10.1016/S0040-4020(97)00559-0
State	Published - Sep 8 1997
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(97)00559-0

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title = "Neighboring the effect in the oxidation of α-Stannyl phenyl vinyl sulfides",

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.",

author = "Glass, {Richard S.} and Qin Guo and Yunqi Liu",

note = "Funding Information: Acknowledgment. Financial support from the National Science Foundation (CHE-9422200) is gratefully acknowledged. The X-ray crystal structure studies reported in this paper were done at the Molecular Structure Laboratory of the University of Arizona. The AM 1 calculations reported in this paper were done by Ms. Abby Parrill in the Department of Chemistry of the University of Arizona.",

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doi = "10.1016/S0040-4020(97)00559-0",

language = "English (US)",

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T1 - Neighboring the effect in the oxidation of α-Stannyl phenyl vinyl sulfides

AU - Glass, Richard S.

AU - Guo, Qin

AU - Liu, Yunqi

N1 - Funding Information: Acknowledgment. Financial support from the National Science Foundation (CHE-9422200) is gratefully acknowledged. The X-ray crystal structure studies reported in this paper were done at the Molecular Structure Laboratory of the University of Arizona. The AM 1 calculations reported in this paper were done by Ms. Abby Parrill in the Department of Chemistry of the University of Arizona.

PY - 1997/9/8

Y1 - 1997/9/8

N2 - 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.

AB - 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.

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JO - Tetrahedron

JF - Tetrahedron

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ER -

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

Abstract

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