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Electrochemical synthesis of isothiocyanogen and its reactivity in thiocyanation reactions Full article

Journal Electrochimica Acta
ISSN: 1873-3859 , E-ISSN: 0013-4686
Output data Year: 2020, Volume: 513, Article number : 145517, Pages count : DOI: 10.1016/j.electacta.2024.145517
Authors Kozyrev Yuriy N. 1 , Mendkovich Andrey S. 1 , Kokorekin Vladimir A. 1,2 , Luzhkov Victor B. 3 , Rusakov Alexander I. 4
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia
2 Sechenov First Moscow State Medical University (Sechenov University), 119991 Moscow, Russia
3 Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, 142432 Chernogolovka, Russia
4 P. G. Demidov Yaroslavl State University, 150000 Yaroslavl, Russia

Abstract: The electrochemical oxidation of (iso)thiocyanic acid was studied for the first time by complex of experimental (cyclic voltammetry, controlled potential electrolysis) and theoretical (digital simulations, quantum chemical calculations) methods. We unexpectedly discovered that electrooxidation of (iso)thiocyanic acid leads to isothiocyanogen (and not to thiocyanogen, as in the oxidation of thiocyanate salts). It is the first case where isothiocyanogen was synthesized in solution under mild conditions. The reactivity of isothiocyanogen has been evaluated using indole thiocyanation as a model reaction. The high yield of 3-thiocyanato-1H-indole (93 %) obtained in this process underscores its practical interest.
Cite: Kozyrev Y.N. , Mendkovich A.S. , Kokorekin V.A. , Luzhkov V.B. , Rusakov A.I.
Electrochemical synthesis of isothiocyanogen and its reactivity in thiocyanation reactions
Electrochimica Acta. 2020. V.513. 145517 . DOI: 10.1016/j.electacta.2024.145517 WOS Scopus OpenAlex
Dates:
Submitted: Sep 25, 2024
Published online: Dec 23, 2024
Identifiers:
≡ Web of science: WOS:001393897100001
≡ Scopus: 2-s2.0-85212848330
≡ OpenAlex: W4405436979
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