3 years ago

A Water-Containing Organopotassium Compound Based on Bis(4,6-tBu-benzoxazol-2-yl)methanide and Its Unexpected Stability to Hydrolysis

A Water-Containing Organopotassium Compound Based on Bis(4,6-tBu-benzoxazol-2-yl)methanide and Its Unexpected Stability to Hydrolysis
Dietmar Stalke, Regine Herbst-Irmer, Ingo Koehne, Sebastian Bachmann
The bulky bis(4,6-tBu-benzoxazol-2-yl)methane ligand system enabled the synthesis of the water-containing organometallic potassium complex [(18-crown-6)K{(4,6-tBu-OCNC6H2)2CH}⋅H2O] (2), which is an unprecedented example of a water-stable reactive organopotassium compound. Furthermore, 2 is a rare example of a bis(benzoxazol-2-yl)methanide ligand displaying solely O-coordination to a metal ion. Compound 2 was fully characterized through its solid-state structure. Furthermore, its behavior in solution was investigated by NMR titration DOSY experiments. These revealed full protonation of the complex only after seven days and the addition of 114 equivalents of water. Fire and water are unified in a solely O-coordinated organopotassium complex based on the ambidentate bis(4,6-tBu-benzoxazol-2-yl)methanide ligand. The complex is fully protonated only after seven days and the addition of 114 equivalents of water, and might turn out to be a sustainable synthetic synthon in deep eutectic solvents.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201706316

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