Related Experiment Video
Updated: Jun 25, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Thiocarbonyl Pseudohalides - The Curious Case of Thiocarbonyl Dithiocyanate
Jonathan Pfeiffer1, Hennes Günther1, Patrick Fuzon1
1Philipps-University of Marburg, Hans-Meerwein-Strasse 4, 35043, Marburg.
Abstract:
Thiocarbonyl dithiocyanate (1) and chlorothiocarbonyl thiocyanate (2) were synthesized from thiophosgene and ammonium or silver thiocyanate, respectivley. Their crystal structures show syn-anti (1) and syn (2) conformations, which were confirmed in the bulk phases by powder X-ray diffraction, vibrational spectroscopy and DFT calculations. Further calculations explain the isolation of the kinetic reaction products by a lower transition states opposed to the thermodynamic reaction products. Reaction of 1 with ethanol gave a dithiobiuret derivative (3). In a proof-of-principle study we show that it in turn can be used for the complexation of nickel to yield (4).
Related Concept Videos
Preparation and Reactions of Thiols
Preparation and Reactions of Sulfides
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution
α-Halogenation of Carboxylic Acid Derivatives: Overview
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

