Synthesis and some transformations of 1-chloro-2,2,2-trifluoroethyl isocyanate

Abstract A convenient synthetic approach for previously unknown 1-chloro-2,2,2-trifluoroethyl isocyanate, based on reaction of easily accessible N-(2,2,2-trifluoroethyl-1-hydroxy)-O-ethylcarbamate with thionyl chloride and/or phosphorus pentachloride, was developed. The synthetic potential of the isocyanate as novel bielectrophilic building block was demonstrated by its easy functionalization with N- and O-centered nucleophiles involving participation of one or both electrophilic centers of the C N C triad.