Synthesis of sterically-hindered 1,7-dicarba-closo-dodecarborane thiourea analogs

We herein report the first successful synthesis of 1-thioisocyanato-1,7-dicarba-closo-dodecarborane, which afforded novel lipophilic thiourea analogs by reacting with weak and bulky nucleophilic amines including 1-adamantylamine, and m-carboranylamine, aniline, and 2-aminopyridine. Newly synthesized thiourea analogs were fully characterized by NMR, ESI-MS, and FTIR.

Efficient strategy to synthesize new and novel sterically-hindered 1,7-dicarba-closo-dodecaborane thiourea analogs was developed by reacting by reacting1-thioisocyanato-1,7-dicarba-closo-dodecarborane with bulky and weak amine nucleophiles.Figure optionsDownload as PowerPoint slideHighlights
► First synthesis of 1-thioisocyanato-1,7-dicarba-closo-dodecarborane.
►  Reaction of m-carboranyl isothiocyanate with weak and bulky amines.
►  Comprehensive characterization of novel thiourea analogs by NMR, ESI-MS and FT-IR.