65673-03-2Relevant academic research and scientific papers
Diamino- and mixed amino-amido-N-heterocyclic carbenes based on triazine backbones
Makhloufi, Abdelaziz,Frank, Walter,Ganter, Christian
, p. 2001 - 2008 (2012/04/23)
The synthesis of novel hexahydrotriazine-based NHCs from easily available starting materials is described. Tribenzyltriazacyclohexane 1 is converted stepwise to the six-membered diamino carbene 3 with a saturated ring structure. Analogously, the cyclic mixed amino-amido carbene 12 is obtained starting from a cyclic urea derivative. Both carbenes were characterized by trapping reactions with sulfur and selenium as well by the preparation of metal complexes of the type (COD)MX-NHC (M = Rh, Ir; COD = 1,5-cyclooctadiene), which were converted to the respective dicarbonyl complexes (CO)2MX-NHC. IR spectra of the carbonyl derivatives allowed the Tolman electronic parameter to be determined for carbenes 3 (2052 cm-1) and 12 (2058 cm-1) and revealed a shift of 6 cm-1 due to the presence of one amide function. X-ray structure determinations are reported for an amidinium species, a carbene sulfide, and the (COD)RhBr complex of the amino-amido carbene 12.
