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<p>Tribromo-, trichloro-, and bromo(dichloro)-substituted 1,3,5-triazidobenzenes react with methanethiolate anion in acetone at 10 °C by a mechanism of concerted nucleophilic aromatic substitution (cS<sub>N</sub>Ar) to give 1,3,5-triazido-2,4-dibromo-6-(methylthio)-benzene, 1,3,5-triazido-2,4-dichloro-6-(methylthio)benzene, 1,3,5-triazido-2-bromo-4,6-bis(methylthio)benzene, 1,3,5-triazido-2-chloro-4,6-bis(methylthio)-benzene, and 1,3,5-triazido-2,4,6-tris(methylthio)benzene. The higher the positive charge on the halogen atoms and the negative charge on the carbon atoms in the C—Hal reaction centers of the starting azides, the more easily proceed the reactions.</p>

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Non-catalytic methylthiolation of perhalogenated 1,3,5-triazidobenzenes to 1,3,5-triazido-2,4,6-tris(methylthio)benzene

  • 期刊论文

  • 发表日期：

    2026年2月1日

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  • E. N. Ushakov,
  • S. V. Chapyshev

摘要

Tribromo-, trichloro-, and bromo(dichloro)-substituted 1,3,5-triazidobenzenes react with methanethiolate anion in acetone at 10 °C by a mechanism of concerted nucleophilic aromatic substitution (cSNAr) to give 1,3,5-triazido-2,4-dibromo-6-(methylthio)-benzene, 1,3,5-triazido-2,4-dichloro-6-(methylthio)benzene, 1,3,5-triazido-2-bromo-4,6-bis(methylthio)benzene, 1,3,5-triazido-2-chloro-4,6-bis(methylthio)-benzene, and 1,3,5-triazido-2,4,6-tris(methylthio)benzene. The higher the positive charge on the halogen atoms and the negative charge on the carbon atoms in the C—Hal reaction centers of the starting azides, the more easily proceed the reactions.