Abstract
The reaction of m-substituted anilines with sulfur monochloride has been studied. It has been shown that cyclization with the formation of 1, 3, 2-benzothiazathiolium compounds takes place in the position para to the substituent. The introduction of methoxy groups into o-nitroanilines interferes with the displacement of the nitro group by the chlorine atom. A nucleophilic reaction mechanism has been proposed according to which the nitro group is displaced after the formation of the thiathioniaazine ring.
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References
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Strelets, B.K., Éfros, L.S. & Todres, Z.V. Orientation and mechanism of reactions of aromatic amines with sulfur monochloride. Chem Heterocycl Compd 6, 327–329 (1970). https://doi.org/10.1007/BF00471234
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DOI: https://doi.org/10.1007/BF00471234