Electrochemical synthesis of isothiocyanogen and its reactivity in thiocyanation reactions

Electrochemical synthesis of isothiocyanogen and its reactivity in thiocyanation reactions Научная публикация

Журнал

Electrochimica Acta
ISSN: 1873-3859 , E-ISSN: 0013-4686

Вых. Данные

Год: 2020, Том: 513, Номер статьи : 145517, Страниц : DOI: 10.1016/j.electacta.2024.145517

Авторы

Kozyrev Yuriy N. ¹ , Mendkovich Andrey S. ¹ , Kokorekin Vladimir A. ^1,2 , Luzhkov Victor B. ³ , Rusakov Alexander I. ⁴

Организации

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

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.

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

Поступила в редакцию:	25 сент. 2024 г.
Опубликована online:	23 дек. 2024 г.

≡ Web of science:	WOS:001393897100001
≡ Scopus:	2-s2.0-85212848330
≡ OpenAlex:	W4405436979