KIT | KIT-Bibliothek | Impressum | Datenschutz

One‐Pot Synthesis of Thiocarbamates

Waibel, Kevin A. 1; Barther, Dennis ORCID iD icon 1,2; Malliaridou, Triantafillia 1,2; Moatsou, Dafni 1,2; Meier, Michael A. R. 1,2
1 Laboratorium für Applikationen der Synchrotronstrahlung (LAS), Karlsruher Institut für Technologie (KIT)
2 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)


An efficient isocyanide-based synthesis of S-thiocarbamates was discovered and thoroughly investigated. The new reaction protocol is a one-pot procedure and allows the direct conversion of N-formamides into thiocarbamates by initial dehydration with p-toluene sulfonyl chloride to the respective isocyanide and subsequent addition of a sulfoxide component. Contrary to recent literature, which also uses isocyanides as starting material, but with other sulfur reagents than sulfoxides, in this protocol, no isolation and purification of the isocyanide component is necessary, thus significantly decreasing the environmental impact and increasing the efficiency of the synthesis. The new protocol was applied to synthesize a library of sixteen thiocarbamates, applying four N-formamides and four commercially available sulfoxides. Furthermore, experiments were conducted to investigate the reaction mechanism. Finally, four norbornene-based thiocarbamate monomers were prepared and applied in controlled ring-opening metathesis polymerization (ROMP) reactions. The polymers were characterized by size-exclusion chromatography (SEC) and their properties were investigated utilizing differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA).

Verlagsausgabe §
DOI: 10.5445/IR/1000137400
Veröffentlicht am 15.09.2021
DOI: 10.1002/ejoc.202100858
Zitationen: 2
Web of Science
Zitationen: 1
Zitationen: 2
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsmonat/-jahr 08.2021
Sprache Englisch
Identifikator ISSN: 1434-193X, 1099-0690
KITopen-ID: 1000137400
HGF-Programm 43.33.11 (POF IV, LK 01) Adaptive and Bioinstructive Materials Systems
Erschienen in European journal of organic chemistry
Verlag John Wiley and Sons
Band 2021
Heft 31
Seiten 4508–4516
Vorab online veröffentlicht am 19.08.2021
Nachgewiesen in Web of Science
KIT – Die Forschungsuniversität in der Helmholtz-Gemeinschaft
KITopen Landing Page