Synthesis of 2,4-Disubstituted Thiophenols and Solid State Structures of Thiocarbamate Precursors


  • Aarón Flores-Figueroa Universidad Nacional Autónoma de México
  • Víctor Arist-M. Universidad Nacional Autónoma de México
  • Daniel Talancón-Sánchez Universidad Nacional Autónoma de México
  • Ivan Castillo Universidad Nacional Autónoma de México


Thiols, thiophenols, thiocarbamates, bulky thiols, X-ray structure


Abstract. A series of thiophenols with different ortho-substituents, 2,4-dimethylthiophenol, 2-tert-butyl- 4-methylthiophenol, and 2-(1-adamantyl)-4-methylthiophenol, which display varying degrees of steric hindrance on the 2-position, was prepared from the corresponding phenols. Initial deprotonation of the phenols was achieved with NaH in dimethoxyethane, followed by treatment with N,N-dimethylthiocarbamoyl chloride, to obtain the O-arylthiocarbamates. Thermolysis of the latter compounds resulted in rearrangement, which yields the desired S-arylthiocarbamates. Finally, reduction of the S-arylthiocarbamates with LiAlH4 in THF, followed by acidic workup, allowed the isolation of the thiophenols. All products were characterized by spectroscopic techniques, and in the case of some of the thiocarbamates the solid state structures were determined by single-crystal X-ray diffraction.


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Author Biographies

Aarón Flores-Figueroa, Universidad Nacional Autónoma de México

Instituto de Química

Víctor Arist-M., Universidad Nacional Autónoma de México

Instituto de Química

Daniel Talancón-Sánchez, Universidad Nacional Autónoma de México

Instituto de Química

Ivan Castillo, Universidad Nacional Autónoma de México

Instituto de Química


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