Реферат: New chalcogen–nitrogen π-heterocycles covering 3,1,2,4-benzothiaselenadiazines, 1,3,2,4-benzodithiadiazines and 1,2,4,3,5-benzotrithiadiazepines were synthesized via the electrophilic cyclization of compounds Ar–N[double bond, length as m-dash]S[double bond, length as m-dash]N–SiMe3 under the action of SeCl2, SeCl4/FeCp2, SCl2 and S2Cl2. Heterocycles obtained were thermolyzed into persistent 2,1,3-benzothiaselenazolyls and 1,2,3-benzodithiazolyls (Herz radicals), which were characterized using EPR spectroscopy and DFT calculations. Reaction of the archetypal 3,1,2,4-benzothiaselenadiazine with SCl2 afforded 2,1,3-benzothiaselenazolium chloride (Herz salt), whereas that of sterically hindered 1,3,2,4-benzodithiadiazine resulted in a complex of the corresponding Herz salt with unexpected carbocycle-chlorinated and non-chlorinated 3,3-dioxides of the starting material, which is a rare example of a molecular complex involving a Herz cation. Formation of the dioxides can be explained through intermediate participation of the benzodithiadiazine radical cation. Hydrolysis of 3,1,2,4-benzothiaselenadiazine or 1,3,2,4-benzodithiadiazine led to Se-(2-aminophenyl)selenosulfate (Se-Bunte salt) or S-(2-aminophenyl)thiosulfate (Bunte salt), respectively.

Библиографическая ссылка: Makarov A.Y. , Volkova Y.M. , Zikirin S.B. , Irtegova I.G. , Bagryanskaya I.Y. , Gatilov Y.V. , Nefedov A.A.
New 3,1,2,4-benzothiaselenadiazines, related π-heterocycles including Herz cations, radicals and molecular complexes, and Bunte salts
New Journal of Chemistry. 2022. V.46. N7. P.3687-3696. DOI: 10.1039/D1NJ05979C WOS Scopus РИНЦ OpenAlex

Даты:

Поступила в редакцию:	16 дек. 2021 г.
Принята к публикации:	19 янв. 2022 г.
Опубликована в печати:	20 янв. 2022 г.

Идентификаторы БД:

Web of science:	WOS:000750491600001
Scopus:	2-s2.0-85125491808
РИНЦ:	48187129
OpenAlex:	W4206051707

Цитирование в БД:

БД	Цитирований
OpenAlex	3
Scopus	3
Web of science	4
РИНЦ	3

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