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Investigation of the Reaction of Dithiocarbamic Acid Salts with Fluorinating Agents

Farhang, Amir Mohammad | 2025

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  1. Type of Document: M.Sc. Thesis
  2. Language: Farsi
  3. Document No: 57878 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Ziyaei Halimejani, Azim
  7. Abstract:
  8. Dithiocarbamates have demonstrated extensive applications as synthetic intermediates in the synthesis of functional groups and heterocyclic rings. These compounds, due to their high nucleophilicity, are capable of reacting with a wide range of electrophiles, including aldehydes, alkyl halides, azo compounds, diazo compounds, and many others, yielding diverse and valuable products. This project aims to investigate the reaction of dithiocarbamate salts with fluorinating agents for the synthesis of thiocarbamoyl fluorides. Initially, dithiocarbamate salts were prepared via the reaction of amines with carbon disulfide and the presence of an inorganic base, followed by their conversion to target compounds using Selectfluor. The thiocarbamoyl fluorides were isolated using column or thin-layer chromatography, and their structures were determined by spectroscopic methods including ¹H NMR, ¹³C NMR, 19F NMR. Under optimized conditions, dithiocarbamate salts based on cyclic and acyclic secondary amines were applied successfully in this protocol. Finally, an efficient, novel, and cost-effective synthetic pathway for the preparation of thiocarbamoyl fluorides were developped which overcome the present methods drawbacks
  9. Keywords:
  10. Dithiocarbamate ; Green Reaction ; Fluorinating Agents ; Trifluoromethylamine ; Thiocarbamoyl Fluoride

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