Interaction of 1,3λ4δ2,2,4-benzodithiadiazines with neutral and charged S-electrophiles: SCl2, C6F5SCl, and NS2+

Interaction of 1,3λ4δ2,2,4-benzodithiadiazines with neutral and charged S-electrophiles: SCl2, C6F5SCl, and NS2+ Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2020, Volume: 56, Number: 7, Pages: 968-972 Pages count : 5 DOI: 10.1007/s10593-020-02760-y

Tags

1,2,4,3,5-benzotrithiadiazepine; 1,3,2,4-benzothiadiazines; benzodithiazolium salts; dithionitronium; pentafluorobenzene-sulfenyl chloride; sulfur dichloride; sulfur-nitrogen heterocycles; tetrasulfur tetranitride

Authors

Makarov A.Y. ¹ , Bagryanskaya I.Y. ¹ , Zhivonitko V.V. ²

Affiliations

1	(Scopus) N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk, 630090, Russian Federation
2	(Scopus) NMR Research Unit, Faculty of Science, University of Oulu, P. O. Box 3000, Oulu, 90014, Finland

[Figure not available: see fulltext.] Reactions of 1,3λ4δ2,2,4-benzothiadiazines with SCl2, C6F5SCl, and [NS2][SbF6] leading to 1,2,3-benzodithiazolium salts (Herz salts) were investigated. The relative rate of reaction with SCl2 significantly depends on the nature of the substituent and its position in the carbocycle. Halogen substituents Cl, Br, and I slow down the reaction, especially if located closely to the heterocycle (positions 5 and 8). In the case of C6F5SCl and R = H, chlorination of the carbocycle and opening of the heterocycle also takes place with the formation of 7-chloro-1,3λ4δ2,2,4-benzothiadiazine and C6F5–S–N=S=N–Ar (Ar = 2-Cl-6-F5C6SC6H3), respectively. In the reaction with NS2+, along with contraction of the heterocycle, also its expansion occurs with the formation of 1,2,4λ4δ2,3,5-benzotrithiadiazepine. © 2020, Springer Science+Business Media, LLC, part of Springer Nature.

Makarov A.Y. , Bagryanskaya I.Y. , Zhivonitko V.V.
Interaction of 1,3λ4δ2,2,4-benzodithiadiazines with neutral and charged S-electrophiles: SCl2, C6F5SCl, and NS2+
Chemistry of Heterocyclic Compounds. 2020. V.56. N7. P.968-972. DOI: 10.1007/s10593-020-02760-y WOS Scopus РИНЦ

Published print:	Jul 1, 2020
Published online:	Aug 21, 2020

Web of science	WOS:000561986600009
Scopus	2-s2.0-85089748561
Elibrary	45353061
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