Anodic oxidation of 1, n-halo(alkylthio)alkanes and 1, n-chloro(alkylsulfinyl)alkanes

Ahmed Aced; Elke Anklam; Klaus Dieter Asmus; Klaus Pohl; Richard S. Glass; L. Kraig Steffen; George S. Wilson

doi:10.1080/10426509008045882

Anodic oxidation of 1, n-halo(alkylthio)alkanes and 1, n-chloro(alkylsulfinyl)alkanes

Ahmed Aced, Elke Anklam, Klaus Dieter Asmus, Klaus Pohl, Richard S. Glass, L. Kraig Steffen, George S. Wilson

Chemistry and Biochemistry

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

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Abstract

Anodic oxidation of l, n-halo(alkylthio)alkanes [X-(CH2)n-S-R, X = CI, Br, I] and 1, n-halo(alkylsulfinyl)alkanes [CI-(CH2)n-S(0)-R] was studied by cyclic voltammetry in anhydrous acetonitrile and by controlled potential electrolyses. The ease of sulfur oxidation was not affected by the alkyl substituents R or the number of methylene groups n in compounds with n > 2. The oxidation of the 1, 2-halo(alkylthio)ethanes (n = 2) occurred at slightly higher potentials. The peak potentials decreased slightly in the order CI > Br > I which is probably due to the electronegativity of the halogen atoms. The investigated anodic oxidation was shown to be a two electron irreversible process. Electrolyses in aqueous acetronitrile led to the corresponding sulfoxides and sulfones in good yields.

Original language	English (US)
Pages (from-to)	53-62
Number of pages	10
Journal	Phosphorus, Sulfur, and Silicon and the Related Elements
Volume	48
Issue number	1-4
DOIs	https://doi.org/10.1080/10426509008045882
State	Published - Mar 1 1990

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Inorganic Chemistry

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@article{f7ae4b85613a4228af3feaffe970a69f,

title = "Anodic oxidation of 1, n-halo(alkylthio)alkanes and 1, n-chloro(alkylsulfinyl)alkanes",

abstract = "Anodic oxidation of l, n-halo(alkylthio)alkanes [X-(CH2)n-S-R, X = CI, Br, I] and 1, n-halo(alkylsulfinyl)alkanes [CI-(CH2)n-S(0)-R] was studied by cyclic voltammetry in anhydrous acetonitrile and by controlled potential electrolyses. The ease of sulfur oxidation was not affected by the alkyl substituents R or the number of methylene groups n in compounds with n > 2. The oxidation of the 1, 2-halo(alkylthio)ethanes (n = 2) occurred at slightly higher potentials. The peak potentials decreased slightly in the order CI > Br > I which is probably due to the electronegativity of the halogen atoms. The investigated anodic oxidation was shown to be a two electron irreversible process. Electrolyses in aqueous acetronitrile led to the corresponding sulfoxides and sulfones in good yields.",

author = "Ahmed Aced and Elke Anklam and Asmus, {Klaus Dieter} and Klaus Pohl and Glass, {Richard S.} and Steffen, {L. Kraig} and Wilson, {George S.}",

note = "Funding Information: E.A. thanks the Deutsche Forschungsgemeinschaft for financial support, Mr. J. Bitter (Max Planck lnstitut Miilheim, FRG) is gratefully acknowledged for recording the 400 MHz-NMR-spectra. The support provided by NATO (travel grant R685/0644)i s gratefully acknowledged.",

year = "1990",

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doi = "10.1080/10426509008045882",

language = "English (US)",

volume = "48",

pages = "53--62",

journal = "Phosphorus, Sulfur, and Silicon and the Related Elements",

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T1 - Anodic oxidation of 1, n-halo(alkylthio)alkanes and 1, n-chloro(alkylsulfinyl)alkanes

AU - Aced, Ahmed

AU - Anklam, Elke

AU - Asmus, Klaus Dieter

AU - Pohl, Klaus

AU - Glass, Richard S.

AU - Steffen, L. Kraig

AU - Wilson, George S.

N1 - Funding Information: E.A. thanks the Deutsche Forschungsgemeinschaft for financial support, Mr. J. Bitter (Max Planck lnstitut Miilheim, FRG) is gratefully acknowledged for recording the 400 MHz-NMR-spectra. The support provided by NATO (travel grant R685/0644)i s gratefully acknowledged.

PY - 1990/3/1

Y1 - 1990/3/1

N2 - Anodic oxidation of l, n-halo(alkylthio)alkanes [X-(CH2)n-S-R, X = CI, Br, I] and 1, n-halo(alkylsulfinyl)alkanes [CI-(CH2)n-S(0)-R] was studied by cyclic voltammetry in anhydrous acetonitrile and by controlled potential electrolyses. The ease of sulfur oxidation was not affected by the alkyl substituents R or the number of methylene groups n in compounds with n > 2. The oxidation of the 1, 2-halo(alkylthio)ethanes (n = 2) occurred at slightly higher potentials. The peak potentials decreased slightly in the order CI > Br > I which is probably due to the electronegativity of the halogen atoms. The investigated anodic oxidation was shown to be a two electron irreversible process. Electrolyses in aqueous acetronitrile led to the corresponding sulfoxides and sulfones in good yields.

AB - Anodic oxidation of l, n-halo(alkylthio)alkanes [X-(CH2)n-S-R, X = CI, Br, I] and 1, n-halo(alkylsulfinyl)alkanes [CI-(CH2)n-S(0)-R] was studied by cyclic voltammetry in anhydrous acetonitrile and by controlled potential electrolyses. The ease of sulfur oxidation was not affected by the alkyl substituents R or the number of methylene groups n in compounds with n > 2. The oxidation of the 1, 2-halo(alkylthio)ethanes (n = 2) occurred at slightly higher potentials. The peak potentials decreased slightly in the order CI > Br > I which is probably due to the electronegativity of the halogen atoms. The investigated anodic oxidation was shown to be a two electron irreversible process. Electrolyses in aqueous acetronitrile led to the corresponding sulfoxides and sulfones in good yields.

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Anodic oxidation of 1, n-halo(alkylthio)alkanes and 1, n-chloro(alkylsulfinyl)alkanes

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