Open Access Open Access  Restricted Access Subscription Access

INTERACTION OF 1,3λ4δ2,2,4-BENZODITHIADIAZINES WITH NEUTRAL AND CHARGED S-ELECTROPHILES: SCl2, C6F5SCl, AND NS2+

Александр Ю. Макаров, Ирина Ю. Багрянская, Владимир В. Живонитко
Cover Image

Abstract


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 7chloro-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.

Authors: Alexander Yu. Makarov*, Irina Yu. Bagryanskaya, Vladimir V. Zhivonitko


Keywords


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

Full Text: PDF (Russian) Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv