title: Trifluoroacetic anhydride-catalyzed oxidation of isonitriles by DMSO: a rapid, convenient synthesis of isocyanates.
abstract: A smooth and efficient oxidation of isonitriles to isocyanates by sulfoxides is catalyzed by trifluoroacetic anhydride. With use of DMSO as the oxidant and 5 mol·% TFAA (dichloromethane, -60 to 0 °C), the process is complete in a few minutes, forming dimethyl sulfide as the only byproduct. The newly formed isocyanates may be used directly or isolated in high purity by solvent evaporation.
authors.affiliation: Department of Chemistry & Chemical Biology, Baker Laboratory, Cornell University , Ithaca, New York 14853-1301, United States.
authors.forename: Hoang V
authors.initials: HV
authors.lastname: Le
authors.forename: Bruce
authors.initials: B
authors.lastname: Ganem
mesh_terms: D000089:Acetic Anhydrides; D002384:Catalysis; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D005463:Fluoroacetates; D017953:Isocyanates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D014269:Trifluoroacetic Acid / Q000737:chemistry
chemical_list: D000089:Acetic Anhydrides; D005463:Fluoroacetates; D017953:Isocyanates; D009570:Nitriles; C017958:trifluoroacetic anhydride; D014269:Trifluoroacetic Acid; D004121:Dimethyl Sulfoxide