Electron-transfer initiated nucleophilic substitution of thiophenolate anion by 1-chloro-substituted 4-(thiazol-2-ylazo)naphthalenes

Electron-transfer initiated nucleophilic substitution of thiophenolate anion by 1-chloro-substituted 4-(thiazol-2-ylazo)naphthalenes

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 init...

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Main Authors: Evgenia Dmitrieva, Xiuling Yu, Horst Hartmann
Format: Article
Language:English
Published: Elsevier 2020-05-01
Series:Electrochemistry Communications
Online Access:http://www.sciencedirect.com/science/article/pii/S1388248120300576
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spelling doaj-80730829431b43f5a9729c8e0524a4d02020-11-25T02:01:45ZengElsevierElectrochemistry Communications1388-24812020-05-01114Electron-transfer initiated nucleophilic substitution of thiophenolate anion by 1-chloro-substituted 4-(thiazol-2-ylazo)naphthalenesEvgenia Dmitrieva0Xiuling Yu1Horst Hartmann2Center of Spectroelectrochemistry, Leibniz Institute for Solid State and Materials Research (IFW Dresden), Helmholtzstrasse 20, 01069 Dresden, GermanyTechnische Universität Dresden, Lehrstuhl für Organische Chemie, Mommsenstrasse 6, 01069 Dresden, GermanyTechnische Universität Dresden, Lehrstuhl für Organische Chemie, Mommsenstrasse 6, 01069 Dresden, Germany; Corresponding author.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: Nucleophilic substitution, Spectroelectrochemistry, Radical anions, Disulfide splitting, Azo compoundshttp://www.sciencedirect.com/science/article/pii/S1388248120300576
collection DOAJ
language English
format Article
sources DOAJ
author Evgenia Dmitrieva
Xiuling Yu
Horst Hartmann
spellingShingle Evgenia Dmitrieva
Xiuling Yu
Horst Hartmann
Electron-transfer initiated nucleophilic substitution of thiophenolate anion by 1-chloro-substituted 4-(thiazol-2-ylazo)naphthalenes
Electrochemistry Communications
author_facet Evgenia Dmitrieva
Xiuling Yu
Horst Hartmann
author_sort Evgenia Dmitrieva
title Electron-transfer initiated nucleophilic substitution of thiophenolate anion by 1-chloro-substituted 4-(thiazol-2-ylazo)naphthalenes
title_short Electron-transfer initiated nucleophilic substitution of thiophenolate anion by 1-chloro-substituted 4-(thiazol-2-ylazo)naphthalenes
title_full Electron-transfer initiated nucleophilic substitution of thiophenolate anion by 1-chloro-substituted 4-(thiazol-2-ylazo)naphthalenes
title_fullStr Electron-transfer initiated nucleophilic substitution of thiophenolate anion by 1-chloro-substituted 4-(thiazol-2-ylazo)naphthalenes
title_full_unstemmed Electron-transfer initiated nucleophilic substitution of thiophenolate anion by 1-chloro-substituted 4-(thiazol-2-ylazo)naphthalenes
title_sort electron-transfer initiated nucleophilic substitution of thiophenolate anion by 1-chloro-substituted 4-(thiazol-2-ylazo)naphthalenes
publisher Elsevier
series Electrochemistry Communications
issn 1388-2481
publishDate 2020-05-01
description 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: Nucleophilic substitution, Spectroelectrochemistry, Radical anions, Disulfide splitting, Azo compounds
url http://www.sciencedirect.com/science/article/pii/S1388248120300576
work_keys_str_mv AT evgeniadmitrieva electrontransferinitiatednucleophilicsubstitutionofthiophenolateanionby1chlorosubstituted4thiazol2ylazonaphthalenes
AT xiulingyu electrontransferinitiatednucleophilicsubstitutionofthiophenolateanionby1chlorosubstituted4thiazol2ylazonaphthalenes
AT horsthartmann electrontransferinitiatednucleophilicsubstitutionofthiophenolateanionby1chlorosubstituted4thiazol2ylazonaphthalenes
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