Unexpected reverse cyclization of 2-mercaptobenzimidazole with chlorotrifluoroethylene and hexafluoropropene

The unusual cyclization mode of 2-mercaptobenzimidazole with chlorotrifluoroethylene and hexafluoropropene has been found. Such unexpected products as 2-chloro-2,3,3-trifluoro-2,3-dihydrobenzimidazo[4,513]thiazole-1,3 and 2-trifluoromethy1-2,3,3-trifluoro-2,3-dihydrobenzimidazo[4,5b]thiazole-1,3 were isolated. The structures of obtained compounds were supported by single crystal X-ray diffraction analysis and the possible reaction route was proposed. (C) 2016 Elsevier B.V. All rights reserved.