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Title: Electron-transfer initiated nucleophilic substitution of thiophenolate anion by 1-chloro-substituted 4-(thiazol-2-ylazo)naphthalenes
Authors: Dmitrieva, E.Yu, X.Hartmann, H.
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Issue Date: 2020
Published in: Electrochemistry Communications Vol. 114 (2020)
Publisher: Amsterdam : Elsevier B.V.
Abstract: In this work, the electrochemical transformation of 5-chloro-2-[(4-chloronaphthalen-1-yl)azo]thiazoles (A) into the corresponding radical anion A·− and its subsequent reaction with diphenyldisulfide (PhSSPh) was studied. It was found that the primarily generated azo anion radical A·− is able to initiate an electron transfer process which converts the disulfide into its thiolate anion PhS−. This anion was subsequently able to substitute the Cl- and H-groups by phenylmercapto moieties in the starting azo compound A. The structures of the phenylmercapto-substituted azo compounds thus generated were confirmed by thin-layer chromatography and mass spectrometry using independently prepared compounds as references.
Keywords: Azo compounds; Disulfide splitting; Nucleophilic substitution; Radical anions; Spectroelectrochemistry; Electron transitions; Electron transport properties; Free radical reactions; Mass spectrometry; Naphthalene; Spectroelectrochemistry; Sulfur compounds; Thin layer chromatography; Azo compound; Diphenyldisulfide; Disulfide splitting; Electrochemical transformation; Electron transfer; Electron transfer process; Nucleophilic substitutions; Radical anions; Negative ions
DDC: 540
License: CC BY-NC-ND 4.0 Unported
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Appears in Collections:Chemie

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