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Benzothiazole compounds. 37. Synthesis and spectral characteristics of 3,3'-disubstituted 2,2'-polymethylenedibenzothiazolium salts

I. Čulák, A. Gáplovský, V. Sutoris, and V. Sekerka

Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, CS-842 15 Bratislava


Abstract: It was ascertained that 2,2'-methylenedibenzothiazole reacts in the first step with CH3I or (CH3)2S04 in enamine form, i.e. 2-(2-benzothiazolinylidenemethyl)benzothiazole gives 2-(2-benzothiazolinylidenemethyl)-3-methylbenzothiazolium iodide, re$p. methylsulfate. 2,2,-Ethylene-, 2,2'-trimethylene-, and 2,2'-tetramethylenedibenzothiazole react with CH3I and (CH3)2S04 under formation of appropriate dibenzothiazolium salts. The structure of reaction products was proved by UV, 1H NMR, and 13C NMR spectro­scopy. The compounds were tested on Triticum aestivum L. as growth-regu­lators. 2-(2-Benzothiazolinylidenemethyl)-3-methylbenzothiazolium methyl­sulfate exhibits a high-noticeable activity, while the activity of 2,2'-ethylenedibenzothiazolium di(methylsulfate) is noticeable.

Full paper in Portable Document Format: 443a381.pdf


Chemical Papers 44 (3) 381–388 (1990)

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