University of Oulu

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+. Chem Heterocycl Comp 56, 968–972 (2020). Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 968–972.

Взаимодействие 1,3λ⁴δ²,2,4-бензодитиадиазинов с нейтральными и заряженными S-электрофилами : SCl₂, C₆F₅SCl и NS₂⁺

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Author: Makarov, Alexander Yu.1; Bagryanskaya, Irina Yu.1; Zhivonitko, Vladimir V.2
Organizations: 1N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk, 630090, Russia
2NMR Research Unit, Faculty of Science, University of Oulu, P. O. Box 3000, Oulu, 90014, Finnland
Format: article
Version: accepted version
Access: embargoed
Persistent link:
Language: Russian
Published: Springer Nature, 2020
Publish Date: 2021-08-21


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 аnd 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.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 968–972.

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Изучены реакции 1,3λ⁴δ²,2,4-бензодитиадиазинов с SCl₂, C₆F₅SCl, и [NS₂][SbF₆], приводящие к солям 1,2,3-бензодитиазолия (солям Херца). Относительная скорость реакции с SCl₂ существенно зависит от природы и положения заместителя в карбоцикле. Галогены Cl, Br и I замедляют реакцию, особенно вблизи гетероцикла (в положениях 5 и 8). В случае C₆F₅SCl и R = H происходит также хлорирование карбоцикла и раскрытие гетероцикла с образованием 7-хлор-1,3λ⁴δ²,2,4-бензодитиадиазина и C₆F₅–S–N=S=N–Ar (Ar = 2-Cl-6-F₅C₆SC₆H₃), соответственно. В реакции с NS₂⁺, наряду с сокращением гетероцикла, происходит его расширение с образованием 1,2,⁴λ4δ²,3,5-бензотритиадиазепина.

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Series: Chemistry of heterocyclic compounds
ISSN: 0009-3122
ISSN-E: 1573-8353
ISSN-L: 0009-3122
Volume: 56
Issue: 7
Pages: 968 - 972
DOI: 10.1007/s10593-020-02760-y
Type of Publication: A1 Journal article – refereed
Field of Science: 116 Chemical sciences
Copyright information: © 2020 Springer Science+Business Media, LLC. This is a post-peer-review, pre-copyedit version of an article published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(7), 968–972. The final authenticated English version is available online at: